Ethinyl Estradiol: Shaping Hormonal Medicine and Beyond

Tracing the Roots: Historical Development

Ethinyl estradiol changed the shape of reproductive healthcare in ways few expected during the twentieth century. Developed out of a quest for reliable hormonal therapy, this synthetic estrogen found its way into medical history through decades of research and innovation. Early chemists studied naturally occurring estrogens like estradiol, but struggled with instability and poor oral bioavailability — problems that pushed scientists like Hans Herloff Inhoffen and Walter Hohlweg to create ethinyl estradiol in the 1930s. Their approach hinged on adding an ethinyl group at the 17-alpha position, allowing the molecule to withstand liver metabolism and remain active in the body longer than natural estrogen. This advancement opened doors for widespread use in oral contraceptives, hormone therapy, and research. Without this chemical tweak, it’s hard to imagine the reliable birth control options or certain cancer treatments available today. Ethinyl estradiol went on to anchor the first combined oral contraceptive in 1960, reshaping family planning and women’s health.

What’s in the Box: Product Overview

Pharmaceutical companies package ethinyl estradiol as a fine, white or almost white crystalline powder, used either as a solo product or in tandem with other hormones, most often progestins. It appears in oral tablets, transdermal patches, and occasionally injectable forms, depending on its intended use. Doses tend to run in micrograms, showing just how potent this compound is, especially compared to other estrogens. Most people come across ethinyl estradiol as part of a fixed-dose combination tablet, a hallmark of modern oral contraceptives. As generic and brand-name products fill the shelves, what differentiates them is the quality of excipients and the reliability of manufacturing rather than the core hormonal ingredient itself. The purity level demanded from manufacturers touches 98-102% by assay, and reputable suppliers accompany their product with detailed certificates of analysis, which doctors and pharmacists trust.

How Ethinyl Estradiol Looks and Reacts: Physical & Chemical Properties

Distinct from natural estradiol, ethinyl estradiol carries a 17-alpha ethynyl group, giving it a formula of C20H24O2. It weighs about 296.40 grams per mole. The material often turns up as a white, crystalline powder, insoluble in water but more receptive to organic solvents like ethanol, acetone, and chloroform. It melts at roughly 182-184°C, and most handling requires care due to its potency and low working concentrations. This molecular adjustment isn’t cosmetic. It disrupts rapid liver breakdown, keeping ethinyl estradiol in circulation and reliably triggering estrogenic responses. These traits explain why minuscule doses do the job of milligrams of older, natural estrogens. The slight boost in lipophilicity from the ethinyl group strengthens its pharmacological bite while offering consistency lacking in previous generations of estrogenic ingredients.

Technical Overview: Specifications & Labeling Demands

Regulators and manufacturers do not treat specifications for ethinyl estradiol lightly. Most products meet identity verification through high-performance liquid chromatography (HPLC), melting point analysis, and microanalysis. Labeling mandates precise reporting of the amount per unit, names and strengths of all ingredients, warnings about use during pregnancy, possible side effects, and storage instructions. Storage commonly suggests protection from light, humidity, and excessive heat — deviations can lead to product breakdown and major risk for patients. Shelf life stretches up to five years under correct storage, something often marked on blister packs and patient leaflets. Many regions, in line with international guidelines, stamp medication packaging with serialization and barcoding to support traceability and prevent counterfeit trade, reflecting lessons learned from decades of misuse and errors.

The Chemistry Behind the Drug: Preparation Methods

Synthesizing ethinyl estradiol involves several careful, technical steps that start from estrone or estradiol. The central move introduces the ethinyl group at the 17α position, a process achieved through alkyne addition, usually using acetylene reagents in the presence of a strong base. The synthesis pathway also includes purification via crystallization, repeated washing, and precise temperature controls. Commercial producers scale this up using reactors with strict containment controls, not only to keep yields high but to guard workers and the environment from trace hormone contamination. What’s stunning is the scale: a few kilograms of ethinyl estradiol feed a market serving millions, requiring skillful process design and adherence to green chemistry to minimize waste.

Going Beyond Synthesis: Chemical Reactions & Possible Modifications

Chemists studying ethinyl estradiol often focus on tweaking either the aromatic ring system or the 17α side chain to dial up or dampen estrogenic activity. Introducing halogens, different alkyl groups, or new side chains creates unique analogs, some more potent or selective than the original. These modifications not only guide drug development, they also steer the synthesis of newer progestins and selective estrogen receptor modulators. Research journals document how ethinyl estradiol resists rapid enzymatic breakdown, but can undergo oxidation and conjugation in the liver, creating metabolites that still possess weak hormonal activity. That’s one reason researchers continue to study its long-term metabolic effects and ways to neutralize active byproducts through pharmaceutical engineering.

What’s in a Name: Synonyms and Product Names

Ethinyl estradiol goes by several names in medical and research circles. Trade names cover products like Estinyl (now discontinued), and the compound powers many fixed-dose brands: Microgynon, Marvelon, Alesse, Yaz, and Loestrin, to name a few. Scientific papers reference it under synonyms such as 17α-ethynylestradiol, EE2, and 17-ethinylestradiol. Knowing these monikers matters, especially when patients search for information or doctors switch prescriptions due to local availability. Missing a synonym can lead to confusion, misdosage, or purchase of the wrong product, so manufacturers work hard to ensure consistent naming on primary and secondary packaging, education materials, and even pharmacovigilance databases.

Guardrails and Guard Duty: Safety & Operational Standards

Handling ethinyl estradiol means maintaining strict safety measures due to its hormonal potency and possible biological effects from low-level exposure. Pharmacists prepare doses while wearing gloves, masks, and sometimes extra protective clothing if dealing with powder or bulk forms. The workplace must limit airborne particles with containment hoods or negative pressure rooms, and every spill gets treated as hazardous waste. Healthcare workers follow prescribed disposal methods, since hormone contamination in water can disrupt local ecosystems and prompt regulatory fines. Labeling carries required warnings about pregnancy, lactation, and certain cancer risks, plus side effects ranging from mild headaches to rare but life-threatening thrombotic events. Governing bodies like the FDA and EMA monitor the quality and safety of products through regular inspections, mandating pharmacovigilance programs that catch post-marketing problems early and enforce recalls when needed.

Filling the Gaps: Application Areas

Few pharmaceuticals match the range of applications covered by ethinyl estradiol. It anchors oral contraceptives, giving people around the globe less stressful, more reliable control over reproduction. Combination hormone replacement therapies rely on its familiarity to treat menopausal symptoms and prevent osteoporosis-related fractures. Some treatments for acne, endometriosis, and polycystic ovarian syndrome also incorporate ethinyl estradiol, offsetting hormonal imbalances that drive these conditions. In rare cases, doctors prescribe it for male-to-female transgender hormone therapy, helping patients achieve secondary sexual characteristics in line with their identity. Even veterinarians use ethinyl estradiol to manage reproductive health in livestock. Not every use leads to equal benefit, and patients deserve collaboration to adjust doses, review drug interactions, and watch for adverse reactions.

Beyond the Clinic: Research & Development Efforts

R&D teams in academia and industry track two broad goals — making ethinyl estradiol safer and exploring alternatives that keep helpful estrogenic effects with fewer drawbacks. Investigators dig into its metabolism, with a focus on understanding minor metabolites and their biological impacts. Some explore new drug delivery routes, like vaginal rings and slow-release patches, aiming to bypass the liver and reduce clotting risks or hormone peaks that lead to unwanted side effects. There’s rising interest in “green” synthesis paths to cut down on harmful byproducts and encourage sustainability. On the digital side, bioinformatics aids in mapping receptor binding, working out which analogs might yield stronger results or avoid triggering cancer risks seen in some populations.

Treading Carefully: Toxicity Research

No matter the benefits, significant research persists on the risks tied to ethinyl estradiol, particularly concerning clotting disorders, stroke, and certain cancers. Large-scale epidemiological studies show low but important risks for deep vein thrombosis, especially among smokers and those with other risk factors. Researchers have identified a modest rise in breast and cervical cancer rates, yet also demonstrate lower rates of endometrial and ovarian cancers with long-term use. Investigators keep running animal studies and reviewing case-control data to untangle whether observed effects stem from ethinyl estradiol itself or the progestin partners commonly mixed with it. Beyond the patient, toxicologists focus on what happens when tiny amounts of the hormone seep into water supplies. Disruption of fish reproductive patterns and possible endocrine effects in wildlife remain worries, prompting governments to invest in more advanced wastewater treatment and better risk management.

Looking Forward: Future Prospects and Challenges

Demand for safer, smarter hormone therapies ensures ethinyl estradiol will remain a fixture in medicine, though not without hurdles. Major pharmaceutical firms devote resources to updating combination therapies that use this estrogen or pave the way for non-estrogen alternatives such as selective estrogen receptor modulators. Efforts also aim toward digital health integration — smart packaging, mobile apps, and AI-supported monitoring— to help patients adhere to dosing schedules and report adverse reactions in real time. Laboratories worldwide test new modifications to the molecule, hoping to maintain the benefits with lower cardiovascular, cancer, or environmental risks. There’s an open field in “green chemistry” innovation for hormone manufacturing, balancing human needs against the growing push to curb pharmaceutical pollution. Only time and rigorous research will reveal the balance between established treatments like ethinyl estradiol and the newer, safer, and more sustainable therapies around the corner.



What is Ethinyl Estradiol used for?

The Role in Birth Control

Many people first hear about ethinyl estradiol at the doctor’s office. The name sounds intimidating, but the concept is pretty simple. It’s a synthetic version of estrogen, the hormone that helps control the menstrual cycle. Doctors pair it with other hormones to create combination birth control pills. These pills have fundamentally changed reproductive health.

Think back to the complexity women faced before modern contraception. Choices ranged from unreliable natural methods to non-medical attempts that rarely worked. Today, with a tiny tablet containing ethinyl estradiol, people plan families, pursue careers, and manage menstrual symptoms. The science behind these pills took decades to refine, pushing accidental pregnancy rates down dramatically. A 2018 CDC report showed that 12.6% of women aged 15-49 in the U.S. relied on oral contraceptives. Pills containing ethinyl estradiol offered a way forward for those needing both effectiveness and convenience.

Treating Menstrual and Hormonal Issues

Ethinyl estradiol doesn’t only prevent pregnancy. Many teens and adults face heavy or irregular periods, painful cramps, or hormonal acne. Doctors often turn to the same ingredient, prescribed in slightly different formulations. My friend Sarah struggled in high school, missing classes because of severe cramps and unpredictable cycles. A few months on a combined oral contraceptive containing ethinyl estradiol, and her symptoms eased to the point she could focus on soccer and her studies.

The reach extends to polycystic ovary syndrome (PCOS) too. PCOS affects up to 10% of women of reproductive age, causing a range of problems from irregular periods to unwanted hair growth. By helping regulate cycles and lower excess androgens, ethinyl estradiol improves quality of life for many who deal with this condition.

Risks and Realities

Like every medication, ethinyl estradiol brings benefits and risks. Anyone picking up a pack of pills should hear about side effects: high blood pressure, headaches, and an increased chance of blood clots, especially for smokers over 35. Family history matters, as do other medications — certain antibiotics, seizure drugs, and even supplements can change how the pill works.

Education makes a huge difference here. Many of us felt awkward asking our parents or doctors about birth control. Digital health resources, school programs, and honest conversations break down those barriers. People deserve clear information to weigh their own risks and benefits.

Access and Cost

Access keeps coming up as a challenge. For some people, insurance pays most of the tab, but for others, cost stays too high. Medicaid and many employer plans in the U.S. cover birth control, but gaps remain. Over-the-counter options, telehealth visits, and generic brands break some of those barriers down. Policy changes that support these efforts can make a real difference for students, single parents, or those living in rural areas.

Ethinyl estradiol isn’t a silver bullet, but it’s an important part of modern medicine. From my experience seeing friends, siblings, and coworkers use these pills for wildly different needs, the core truth is this: The option to control one’s body and health opens up a life with more freedom and stability. Transparent, science-backed guidance should be the baseline.

What are the common side effects of Ethinyl Estradiol?

Realities People Face With Ethinyl Estradiol

Ethinyl estradiol shows up in a wide range of birth control pills. Most people expect it to stop pregnancy, regulate cycles, and clear up acne. What tends to get less attention: the everyday side effects that come with using it. With years of listening to friends, patients, and stories online, there is a set of side effects people commonly go through, no matter where they live or how old they are.

Sore Breasts and Nausea: Less Talked About, Really Common

Plenty of women start to notice breast tenderness in the first weeks. It can get in the way at the gym, during sleep, or just by going about regular routines. Nausea is another guest, sometimes strong enough in the morning to get mistaken for pregnancy. These issues rarely last forever, but the adjustment period leaves people feeling uncomfortable as their body gets used to the hormone.

Mood Swings: Not Just in the Movies

Fluctuating hormones don’t just stay in the body. They affect the mind too. Many women talk about feeling more emotional than usual. Sad feelings arrive without warning, irritation spikes, or the typical stress just seems heavier. Harvard Medical School and Mayo Clinic back up these experiences, pointing to estrogen’s power over serotonin, a key brain chemical that controls mood.

Spotting, Weight Changes, and Headaches

Breakthrough bleeding or spotting often takes people by surprise. Even on schedule, some find tiny amounts of blood on underwear between periods, which often causes concern. For some, the scale moves up. Estrogen can lead to mild fluid retention that feels like bloating or adds a couple of extra pounds. I’ve watched friends try everything to control it—less salt, more water, extra workouts. These changes tend to level out, but the frustration is real. Headaches, especially migraines, may also increase. The risk worsens in people who already battle migraines, according to Johns Hopkins research.

Impact on Blood Pressure and Clotting Risk

Most people don’t think twice about blood clots, but this is where careful attention matters. Ethinyl estradiol can increase the risk of deep vein thrombosis and other clots, as the CDC and FDA warn. These cases are rare, but real. Smokers, older women, and those with clotting disorders should always check with a medical professional before starting anything prescription. Slight bumps in blood pressure can also follow long-term use, though annual doctor visits catch these changes early.

What Can Make Side Effects Easier to Handle?

Doctors recommend starting with the lowest possible dose, and following up a month or two later to see how things are going. Reporting anything out of the ordinary—pain in the leg, shortness of breath, vision changes—right away reveals problems quickly. Small changes in lifestyle also help. Daily walks, extra sleep, and hydration can ease mood issues and bloating. Support groups, even on platforms like Reddit, offer tips and real-life solutions that medical literature sometimes skips.

Listening to Each Person’s Experience

No medicine comes without risk, and listening to stories firsthand helps prevent surprises. Ethical health writers and doctors agree: look at individual experiences alongside clinical studies. With Ethinyl estradiol, the most important step is staying honest with yourself and your healthcare provider if something feels off. That’s not just common sense—that’s how health choices get better over time.

How should I take Ethinyl Estradiol?

Understanding the Pill on Your Terms

Doctors prescribed Ethinyl Estradiol for birth control, hormone therapy, or to address menstrual concerns. For many, it’s just another tiny tablet in the daily routine. Still, getting the most out of this medication relies on more than just swallowing a pill—it leans on trust, routine, and accurate information. I remember sitting in the clinic, prescription in hand, realizing I needed more than a schedule. I needed to know how small habits, skipped doses, and even my morning coffee could affect this medication's work inside my body.

Routine Is Everything

Consistency shapes how well Ethinyl Estradiol works. Missing a day can throw the whole system off, translating to unexpected spotting, mood swings, or lower effectiveness for contraception. Those old pill containers with days of the week stamped on them really do make a difference. Try pairing the pill with another part of your daily life—slipping it next to your toothbrush or keeping it in your work bag. Skipping doses, doubling up haphazardly, or taking it at wildly different times only invites confusion and reduces what little control this medicine offers for health and planning.

Food, Health, and Real-World Factors

Some people ask if breakfast matters, or if coffee and vitamins change the impact. Ethinyl Estradiol doesn’t demand a specific meal, but it’s smart to avoid taking it alongside medications that could interfere, like certain antibiotics or anti-seizure drugs. Grapefruit, oddly enough, can sometimes meddle with how hormones get processed in the liver. It’s important to talk to a healthcare professional before introducing anything new to your routine, whether it’s an herbal tea or an over-the-counter supplement.

Know What to Watch For

There’s plenty of chatter online about side effects, but not enough about recognizing what matters most. Sharp leg pain, chest discomfort, and sudden vision changes signal the need for real attention. These aren’t just “bad days”—they could point to blood clots, a rarely advertised risk that deserves respect. Most side effects, like mild nausea or spotting for new users, ease after a couple of cycles. Still, any reaction that creates doubt in your mind should prompt a conversation with your provider. No embarrassment, no waiting—your health history changes the equation, especially if you smoke or have migraines with aura.

Trusting Facts, Not Myths

One person swears Ethinyl Estradiol causes weight gain or mood shifts in all users. For most people, shifts are subtle, if they show up at all. Reliable studies report that body changes often arise from lifestyle, stress, or diet, not the pill. It’s tempting to blame every new ache on something you can pick up from the pharmacy counter, but honest communication with your provider uncovers what’s truly going on. Your doctor didn’t just hand you a prescription; they offered you a tool, and your lived experience teaches you far more than any online rumor.

Building Better Systems

Long-term health means setting up a support network of reminders, regular check-ins, and open conversations. Mobile apps, pill packs, even simple sticky notes on a bathroom mirror have helped folks stay on track. I learned that asking questions makes me a better participant in my own care. Speaking up about strange new symptoms or asking about interactions sometimes heads off big problems down the road. In my own experience, the sense of control comes from turning medication into a habit, fueled by real knowledge—never just guesswork or blind trust.

Are there any medications that interact with Ethinyl Estradiol?

Understanding Ethinyl Estradiol in Everyday Life

Ethinyl estradiol lands in a lot of daily routines. People who rely on combination birth control pills, hormone therapy, or even treatments tied to acne, come across it regularly. It’s smart to recognize how easily outside medications can meddle with how this synthetic estrogen works. I’ve seen many folks surprised to discover their supplement or prescription isn’t as independent as they once believed.

Common Medications That Trigger Change

One group that consistently comes up in discussions: antibiotics, especially rifampin. In my own practice, several women shared stories about missed periods and unexpected spotting after a round of antibiotics. Rifampin stands out—it ramps up liver enzymes that break down ethinyl estradiol, sometimes dropping contraception protection. Not all antibiotics behave this way, yet medical providers still debate over links involving other antibiotics, like ampicillin or tetracycline.

Another adversary: certain anti-seizure or antiepileptic medications, such as phenytoin, carbamazepine, and phenobarbital. These raise liver enzyme activity, so the hormone clears faster from the body. Women balancing seizure control and contraception run into a real puzzle. Careful planning is crucial—the pill doesn't work as well when these drugs speed up how fast estrogen leaves the bloodstream.

Herbal and Over-the-Counter Interactions

Herbal supplements can trick even the most cautious person. St. John’s Wort, commonly used to lift mood, also joins the crowd that ramps up liver enzymes. I’ve overheard conversations at pharmacies where this surprise left people with consequences they never bargained for—sometimes a pregnancy scare, other times just a migraine of confusion. Always ask before mixing herbs or supplements with hormones, since the outcomes aren’t always obvious until trouble appears.

More Than Pills: HIV Medications and Antifungals

Living with HIV means juggling multiple prescriptions, including antiretrovirals like ritonavir. This drug can push and pull hormone levels unpredictably, so birth control protection varies. Some antifungals—like griseofulvin—move in the same direction, lowering the power of the pill and increasing the chance for surprise pregnancy or irregular bleeding.

Everyday Factors: Grapefruit Juice and Smoking

Not every interaction sits behind the pharmacy counter. Grapefruit juice, which seems harmless, can block enzymes and actually boost hormone levels unexpectedly. Smoking, already bad for health in plenty of ways, increases risks when combined with estrogens. Over time, it raises the risk of blood clots, so smokers and anyone over 35 must think twice about pill choices.

Solutions—Trust and Teamwork

Any time there’s a change in your medicine cabinet, remember to check in with a pharmacist or provider. Electronic records help, but honest, face-to-face conversations catch more slip-ups. Keeping a list of current medicines—including those that seem small—protects against surprise interactions. Every detail, no matter how trivial it feels, matters. Families, doctors, and pharmacists working together can stop most of the heartbreak tied to medicine mix-ups.

No pill stands alone. Pharmacy shelves and kitchen counters fill up fast, but what sits there usually works better in harmony, not in competition. That simple truth can sidestep much bigger problems later down the line.

Can Ethinyl Estradiol be used during pregnancy or breastfeeding?

What Ethinyl Estradiol Actually Does

Ethinyl estradiol pops up in a stack of birth control pills and some hormone therapies. As a synthetic estrogen, doctors trust it to help manage everything from menstrual issues to acne. For people who don't want to become pregnant, it offers reliable contraception. That sounds good—until a positive pregnancy test enters the picture.

What Happens if Someone Takes It During Pregnancy?

Taking ethinyl estradiol during pregnancy raises a problem. Decades of research point to the risk of harm to the developing baby. According to the FDA and major professional groups, ethinyl estradiol isn't safe here. It crosses the placenta. That means the baby gets exposed to extra hormones at a sensitive stage. Data from studies link that exposure to birth defects, especially with the reproductive tract and urinary system.

Most gynecologists share stories about patients who found out they were pregnant after weeks or months of using the pill. While a brief slip early on doesn't always lead to visible issues, the consensus holds: staying on estrogen-based pills carries unnecessary risk. It’s not worth gambling with a child's chances before birth, especially when healthier alternatives exist.

What About Taking It While Breastfeeding?

A new baby brings its own challenges, and breastfeeding mothers have extra to think about. Ethinyl estradiol passes into breast milk, and the impact on a nursing infant matters. The levels secreted tend to be low, but even that small trace can reduce breast milk supply. As anyone who’s tried to breastfeed knows, milk supply causes enough stress—no one wants pills getting in the way. There’s evidence from the World Health Organization and American Academy of Pediatrics: better avoid combined hormonal birth control with high estrogen right after giving birth.

Progestin-only pills, or “mini-pills,” offer a safer path. Doctors often recommend them for people who want to avoid pregnancy after delivery. They protect from another pregnancy and don’t dry up milk like estrogen-heavy versions.

Why the Warnings Matter

It’s not about stirring up anxiety. These restrictions save lives. Drug safety relies on years of crowd-sourced medical wisdom, real cases, and lab results. Decades ago, experts learned the hard way that many drugs carry risks unseen at first glance. Ethinyl estradiol can tip the balance in hormone-sensitive moments like pregnancy or early nursing. No parent wants extra worries at these times.

The advice sounds blunt: skip ethinyl estradiol when pregnant or breastfeeding. Not all contraceptives add stress, and the right medical team knows how to keep everyone well.

Looking For Solutions That Put People First

Better awareness helps families avoid accidental exposure. Doctors, nurses, and pharmacists have a job: clear up confusion about which medications fit safe life stages. Pregnant and nursing folks deserve choices that don’t put babies at risk. For those worried about accidental use, bringing up any recent medication with a doctor breaks the cycle of uncertainty. Unplanned pregnancies, missed doses, and surprise breastfeeding hurdles all remind us that real-world health care involves steady communication and support—not complicated, risky pills.

Ethinyl Estradiol
Names
Preferred IUPAC name (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Other names 17α-Ethynylestradiol
EE
Ethinylestradiolum
Ethynyloestradiol
17-Ethynylestradiol
Pronunciation /ɛˈθɪnɪl ɛˈstrædiɒl/
Preferred IUPAC name (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Other names EE
17α-ethynylestradiol
17α-EE
Ethinyloestradiol
19-Norpregna-1,3,5(10)-trien-20-yne-3,17β-diol
17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol
Pronunciation /ɛˌθɪnɪl ɛsˈtrædiːɒl/
Identifiers
CAS Number 57-63-6
Beilstein Reference 3544740
ChEBI CHEBI:27794
ChEMBL CHEMBL: CHEMBL1423
ChemSpider 5373
DrugBank DB00977
ECHA InfoCard ECHA InfoCard: 100.017.783
EC Number 200-342-2
Gmelin Reference Ethinyl Estradiol Gmelin Reference: **83286**
KEGG C01572
MeSH D004967
PubChem CID 2734
RTECS number KI5775000
UNII KH7C070Y4B
UN number UN2811
CAS Number 57-63-6
Beilstein Reference 1911042
ChEBI CHEBI:27797
ChEMBL CHEMBL1423
ChemSpider 14121
DrugBank DB00977
ECHA InfoCard 03ca0b86361d-47ed-8362-c8305d5b60cc
EC Number 200-342-2
Gmelin Reference Gmelin Reference: "81808
KEGG C01828
MeSH D004967
PubChem CID 2734
RTECS number KB2975000
UNII 9473SXD4XC
UN number UN2811
Properties
Chemical formula C20H24O2
Molar mass 296.381 g/mol
Appearance White or almost white crystalline powder
Odor Odorless
Density 1.3 g/cm³
Solubility in water Slightly soluble
log P 3.67
Vapor pressure 1.3 × 10⁻⁸ mmHg (25 °C)
Acidity (pKa) 10.4
Basicity (pKb) 20.79
Magnetic susceptibility (χ) -77.5×10⁻⁶ cm³/mol
Refractive index (nD) 1.595
Viscosity Viscous liquid
Dipole moment 2.35 D
Chemical formula C20H24O2
Molar mass 296.40 g/mol
Appearance White or almost white crystalline powder
Odor Odorless
Density DENSITY: 1.3 g/cm3
Solubility in water Slightly soluble
log P 3.67
Vapor pressure 4.5 x 10^-8 mmHg
Acidity (pKa) 15.1
Basicity (pKb) 4.01
Magnetic susceptibility (χ) -76.7×10⁻⁶ cm³/mol
Refractive index (nD) 1.591
Viscosity Viscosity: 0.548 cP
Dipole moment 2.37 D
Thermochemistry
Std molar entropy (S⦵298) Std molar entropy (S⦵298) of Ethinyl Estradiol is 505.7 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -147.6 kJ/mol
Std molar entropy (S⦵298) Std molar entropy (S⦵298) of Ethinyl Estradiol is 540.3 J·mol⁻¹·K⁻¹
Std enthalpy of combustion (ΔcH⦵298) -36238 kJ/mol
Pharmacology
ATC code G03CA01
ATC code G03CA01
Hazards
Main hazards May cause cancer; suspected of damaging fertility or the unborn child; causes skin and serious eye irritation; may cause respiratory irritation.
GHS labelling GHS02, GHS07, GHS08
Pictograms GHS07, GHS08
Signal word Warning
Hazard statements H351: Suspected of causing cancer.
Precautionary statements P201, P273, P281, P308+P313, P405, P501
NFPA 704 (fire diamond) 1-1-0-ALK
Flash point '186.6 °C'
Autoignition temperature 400°C
Lethal dose or concentration LD50 (rat, oral): 5 mg/kg
LD50 (median dose) LD50: 480 mg/kg (oral, rat)
NIOSH RT8750000
PEL (Permissible) 0.1 mg/m³
REL (Recommended) 0.03 mg
IDLH (Immediate danger) Unknown
Main hazards May cause cancer; causes damage to fertility or the unborn child; harmful if swallowed; causes serious eye irritation
GHS labelling GHS02, GHS07, GHS08
Pictograms GHS07
Signal word Warning
Hazard statements H351: Suspected of causing cancer. H360FD: May damage fertility. May damage the unborn child. H362: May cause harm to breast-fed children. H413: May cause long lasting harmful effects to aquatic life.
Precautionary statements P201, P202, P264, P270, P280, P308+P313, P405, P501
NFPA 704 (fire diamond) Health: 2, Flammability: 1, Instability: 0, Special: -
Flash point 167.6°C
Autoignition temperature > 385 °C
Lethal dose or concentration LD50 (oral, rat): 480 mg/kg
LD50 (median dose) LD50 (median dose): 9600 µg/kg (oral, rat)
PEL (Permissible) PEL: Not Established
REL (Recommended) 30 µg
Related compounds
Related compounds Estradiol
Mestranol
Estriol
Ethinylestradiol sulfate
17α-Ethinylestradiol-3-sulfate
Estrone
Quinestrol
Dienestrol
Related compounds Estradiol
Mestranol
Ethinylestradiol sulfate
17α-Ethynylestradiol 3-methyl ether
17α-Ethynylestradiol 3-acetate