3D Mol Similar

β-ESTRADIOL

Iupac Name：(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

CAS No.: 50-28-2

Molecular Weight：272.38196

Modify Date.: 2023-04-06 22:23

Introduction: Potent mammalian estrogenic hormone produced by the ovary. View more+

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1. Names and Identifiers

1.1 Name: β-ESTRADIOL
1.2 Synonyms: (+)-3,17b-Estradiol (+)-3,17Β-Estradiol (17b)-estra-1(10),2,4-triene-3,17-diol (17b)-Estra-1,3,5(10)-triene-3,17-diol (17Β)-Estra-1(10),2,4-triene-3,17-diol (8R,9S,13S,14S,17S)-13-Methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3,17-diol 1,3,5-Estratriene-3,17beta-diol 1,3,5-Estratriene-3,17Β-diol 13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol 13Β-Methyl-1,3,5(10)-gonatriene-3,17Β-ol 17b-Estradiol 17-Beta-Estradiol 17beta-Estradiol 17BETA-ESTRADIOL-16,16,17-D3 17b-Oestra-1,3,5(10)-triene-3,17-diol 17b-Oestradiol 17b-OH-estradiol 17b-OH-oestradiol 17Β estradiol 17Β estradiol (E2) 17-Β-estradiol 17Β-estradiol 17Β-Oestradiol 17-Β-OH-estradiol 17Β-OH-estradiol 17-Β-OH-oestradiol 17Β-OH-oestradiol 3,17b-Dihydroxy-1,3,5(10)-oestratriene 3,17b-Dihydroxyestra-1,3,5(10)-triene 3,17b-Estradiol 3,17beta-Dihydroxy-1,3,5(10)-estratriene 3,17b-Oestradiol 3,17Β-Dihydroxyestra-1,3,5(10)-triene 3,17Β-Estradiol B-Estradiol BETA-ESTRADIOL-16,16,17-D3 D-3,17b-Estradiol D-3,17b-Oestradiol D-3,17Β-Estradiol Destradiol Dihydrofolliculin EINECS 200-023-8 Epiestriol 50 estra-1(10),2,4-triene-3,17-diol, (17b)- Estra-1(10),2,4-triene-3,17-diol, (17Β)- Estra-1,3,5(10)-triene-3,17b-diol Estra-1,3,5(10)-triene-3,17-diol(17b)- Estra-1,3,5(10)-triene-3,17-diol, (17Β)- Estra-1,3,5-triene-3,17-diol Estradiol estradiol 17b Estradiol, Β- Estradiol-17 Β Estradiol-17b Estradiol-17Β Estradiol-17-Β Estradiol-3,17b Estradiolo [DCIT] Estradiolum Estrogel FEMPATCH MFCD01074033 Oestra-1,3,5(10)-triene-3,17b-diol Oestra-1,3,5(10)-triene-3,17Β-diol Oestradiol-17b Oestradiol-17Β Oestrogel Ovocylin Profoliol B Δ-Estradiol Δ-Oestradiol

1.3 CAS No.: 50-28-2

1.4 CID: 5757

1.5 EINECS(EC#): 200-023-8

1.6 Molecular Formula: C18H24O2 (isomer)

1.7 Inchi: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

1.8 InChkey: VOXZDWNPVJITMN-ZBRFXRBCSA-N

1.9 Canonical Smiles: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O

1.10 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O

2. Properties

2.1 Density: 1.17

2.1 Melting point: 173℃

2.1 Boiling point: 445.9°Cat760mmHg

2.1 Refractive index: 1.599

2.1 Flash Point: 209.6°C

2.1 Precise Quality: 272.17800

2.1 PSA: 40.46000

2.1 logP: 3.60920

2.1 Appearance: white to off-white crystalline powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: White or almost white, crystalline powder or colourless crystals.

2.4 Color/Form: Prisms from 80% alcohol
White or slightly yellow, small crystals or crystalline powder

2.5 Contact Allergens: Natural estradiol, used in transdermal systems for hormonalsubstitution, can induce allergic contact dermatitis,with the risk of systemic contact dermatitis afteroral reintroduction.

2.6 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.7 Odor: Odorless

2.8 pKa: pKa 10.71±0.02(H2O(0.1% p-dioxane) t=25±0.1 I=0.03(KCl))(Approximate)

2.9 Water Solubility: [3.6]

2.10 Spectral Properties: Specific optical rotation at 25 deg C for D (sodium) line: +76 deg to +83 deg (dioxane); UV max: 225, 280 nm.

2.11 Stability: Stable. Incompatible with strong oxidizing agents.

2.12 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The 17beta-isomer of estradiol.

3.2 Potential Exposure: The working environment may becontaminated during sex hormone manufacture, especiallyduring the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powderedproducts and recrystallization. Airborne particles of sexhormones may be absorbed through the skin, ingested orinhaled. Enteric absorption results in quick inactivation ofsex hormones in the liver. The rate of inactivation isdecreased for the oral, alkylated steroid hormones (methyltestosterone, anabolic steroids, etc.). Sex hormones mayaccumulate and reach relatively high levels even if theirabsorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health.Intoxication by sex hormones may occur in almost all theexposed workers if preventive measures are not taken. Theeffect in the industrial sector is more successful thanthe agricultural one (chemical caponizing of cockerels bystilbestrol implants and incorporation of estrogens in feedfor body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger

3.3 Shipping: UN3249 Medicine, solid, toxic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials

3.4 Usage: Potent mammalian estrogenic hormone produced by the ovary.

4. Safety and Handling

4.1 Symbol: GHS08;

4.1 Hazard Codes: T

4.1 Signal Word: DANGER

4.1 Risk Statements: R45

4.1 Safety Statements: S53;S45

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow = 4.01 /B-estradiol/

4.3 Other Preventative Measures: WORKROOMS MUST BE KEPT VERY CLEAN, & CONTAMINATED CLOTHING SHOULD BE DESTROYED OR CLEANED. ... COMPLETE PREVENTION OF ENVIRONMENTAL POLLUTION IS NEVERTHELESS NOT EASY, BECAUSE OF PERSISTENCE OF LIGHT POWDER IN AIR. WORKER MUST THEREFORE CO-OPERATE IN PREVENTION OF CHRONIC INTOXICATION ... . /ESTROGENS/

4.4 Hazard Class: 6.1

4.4 Hazard Declaration: H351; H360Fd; H362

4.4 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.5 RIDADR: HAZARD

4.5 Safety Profile: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A promoter. Human reproductive effects by ingestion: ferthty effects. Experimental reproductive effects. Human mutation data reported. A steroid hormone much used in medicine. When heated to decomposition it emits acrid smoke and irritating fumes.

4.6 Caution Statement: P201-P263-P281-P308 + P313

4.6 Formulations/Preparations: Grade: NF (beta-form)
Commonly used preparations are the benzoate, dipropionate, and valerate, as well as ethinylestradiol.

4.7 WGK Germany: 3

4.7 RTECS: KG2975000

4.7 Report: NTP 10th Report on Carcinogens.?IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 279; IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 99.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

4.8 Safety: Hazard Codes:T
Risk Statements:60-61-45-63
60:May impair fertility
61:May cause harm to the unborn child
45:May cause cancer
63:Possible risk of harm to the unborn child
Safety Statements:53-22-36/37/39-45
53:Avoid exposure - obtain special instruction before use
22:Do not breathe dust
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR:2811
WGK Germany:3
HazardClass:6.1
PackingGroup:III
Hazardous Substances Data:50-28-2(Hazardous Substances Data)

4.9 Specification

The Estradiol with the cas number 50-28-2, is also called (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol named by IUPAC. Its' system names are (1) 17beta-Estradiol ; (2) Estra-1,3,5(10)-triene-3,17-diol (17beta)- ; (3) Estra-1,3,5(10)-triene-3,17-diol, (17beta)-. And it belongs to the following product categories: (1)Steroids; (2)Estrogen; (3)Hormone; (4)Analytical Chemistry; (5)Biochemistry; (6)Environmental Endocrine Disruptors; (7)Estradiol, etc. (Environmental Endocrine Disruptors); (8)Hydroxysteroids; (9)Intracellular receptor. It seems like off-white to pale yellow solid, and it is better to store Estradiol around 2-8°C. It is stable, however, it is incompatible with strong oxidizing agents.

Physical properties about 19-Norethisterone are: (1)ACD/LogP: 4.13 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 4.13 ; (4)ACD/LogD (pH 7.4): 4.13 ; (5)ACD/BCF (pH 5.5): 811.75 ; (6)ACD/BCF (pH 7.4): 810.7 ; (7)ACD/KOC (pH 5.5): 4208.86 ; (8)ACD/KOC (pH 7.4): 4203.38 ; (9)#H bond acceptors: 2 ; (10)#H bond donors: 2 ; (11)#Freely Rotating Bonds: 2 ; (12)Polar Surface Area: 18.46?² ; (13)Index of Refraction: 1.599 ; (14)Molar Refractivity: 79.5 cm³ ; (15)Molar Volume: 232.6 cm³ ; (16)Polarizability: 31.51 ×10^-24cm³ ; (17)Surface Tension: 48.9 dyne/cm ; (18)Density: 1.17 g/cm³ ; (19)Flash Point: 209.6 °C ; (20)Enthalpy of Vaporization: 74.19 kJ/mol ; (21)Boiling Point: 445.9 °C at 760 mmHg ; (22)Vapour Pressure: 9.82E-09 mmHg at 25°C

Uses of Estradiol: It is a sex hormone, also called oestradiol. Estradiol is the predominant sex hormone present in females. It is also present in males, being produced as an active metabolic product of testosterone. In the female, estradiol acts as a growth hormone for tissue of the reproductive organs, supporting the lining of the vagina, the cervical glands, the endometrium, and the lining of the fallopian tubes. It enhances growth of the myometrium. Furthermore, the development of secondary sex characteristics in women is driven by estrogens, to be specific, estradiol. The effect of estradiol (and estrogens) upon male reproduction is complex. There is evidence that estradiol functions to prevent apoptosis of male sperm cells.

Besides, several studies have noted that sperm counts have been declining in many parts of the world and it has been postulated that this may be related to estrogen exposure in the environment. Suppression of estradiol production in a subpopulation of subfertile men may improve the semen analysis. There is evidence that estradiol has a profound effect on bone. Women past menopause experience an accelerated loss of bone mass due to a relative estrogen deficiency. Also, Estradiol has complex effects on the liver. It can lead to cholestasis. It affects the production of multiple proteins including lipoproteins, binding proteins, and proteins responsible for blood clotting. EspecialLy, Estrogen is considered to play a significant role in women’s mental health, with links suggested between the hormone, mood and well-being. Sudden drops or fluctuations in, or long periods of sustained low levels of estrogen may be correlated with significant mood-lowering. Clinical recovery from depression postpartum, perimenopause, and postmenopause was shown to be effective after levels of estrogen were stabilized and/or restored.

Production of? Estradiol. 1.During the reproductive years, most estradiol in women is produced by the granulosa cells of the ovaries by the aromatization of androstenedione (produced in the theca folliculi cells) to estrone, followed by conversion of estrone to estradiol by 17β-hydroxysteroid reductase. Smaller amounts of estradiol are also produced by the adrenal cortex, and (in men), by the testes. 2. Estradiol is not only produced in the gonads: in both sexes, precursor hormones, specifically testosterone, are converted by aromatization to estradiol. In particular, fat cells are active to convert precursors to estradiol, and will continue to do so even after menopause. Estradiol is also produced in the brain and in arterial walls.

When you are using this chemical, please be cautious about it as the following: It may impair fertility. And may cause harm or Possible risk of harm to the unborn child. Besides, it may also cause cancer. When you are using this product, wear suitable protective clothing, gloves and eye/face protection. In addition, avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure :
(1).SMILES: Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C
(2).InChI:InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

Toxic information of Estradiol can be showed as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD	subcutaneous	> 300mg/kg (300mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.

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4.10 Toxicity: LD50 subcutaneous in rat: > 300mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Reproductive toxicity, Category 1A

Reproductive toxicity, Additional category for effects on or via lactation

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H351 Suspected of causing cancer H360 May damage fertility or the unborn child H362 May cause harm to breast-fed children
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P263 Avoid contact during pregnancy and while nursing. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

50-28-2Total: 131 Synthesis Route

53-16-7 432 Suppliers

50-28-2 487 Suppliers

Literatures:
Wang, Bijia; Qin, Linlin; Neumann, Kiel D.; Uppaluri, Shriharsha; Cerny, Ronald L.; DiMagno, Stephen G. Organic Letters, 2010 , vol. 12, # 15 p. 3352 - 3355
Yield: ~97%

57-91-0 137 Suppliers

50-28-2 487 Suppliers

Literatures:
Schering Corp. Patent: US2225419 , 1938 ; Full Text Show Details Schering A.G. Patent: DE705314 , 1937 ; DRP/DRBP Org.Chem.
Yield: null

64-17-5 400 Suppliers

50-28-2 487 Suppliers

Literatures:
Schering-Kahlbaum A.G. Patent: GB428133 , 1933 ; Full Text Show Details Schering A.G. Patent: DE711378 , 1932 ; DRP/DRBP Org.Chem.
Yield: null

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8. Precursor and Product

precursor:

64-17-5

846-48-0

1035-77-4

63-05-8

57-63-6

141-52-6

434-22-0

1068-56-0

6045-51-8

4954-14-7

3233-70-3

901-93-9

53-16-7

791-69-5

57-91-0

View all

product :

15270-30-1

362-07-2

123715-80-0

362-05-0

979-32-8

1150-90-9

122566-22-7

5976-61-4

2487-49-2

1743-60-8

10427-24-4

217792-89-7

128965-87-7

53-16-7

1089-78-7

3571-53-7

313-06-4

26788-23-8

6936-94-3

16205-32-6

20823-11-4

3583-03-7

26584-90-7

3398-11-6

6298-51-7

19590-55-7

View all

9. Other Information

9.0 Usage: β-Estradiol is the major estrogen secreted by the premenopausal ovary. It acts as an estrogenic hormone receptor (ER) agonist and activator of PI 3-kinase. Further, it is used in the treatment of infertility in women, prostate cancer and breast cancer. It is also employed as an agent of stimulating female puberty induction, as in the treatment of delayed puberty caused by hypogonadism or Turner's syndrome. In addition to this, it is used as part of the hormone replacement therapy for transgender women.

10. Computational chemical data

Molecular Weight: 272.38196g/mol
Molecular Formula: C₁₈H₂₄O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 272.177630004
Monoisotopic Mass: 272.177630004
Complexity: 382
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.5
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDBAAAAGgAACAAADxSgmAIyBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgINiKCERKAcAAkwBEImAeAwPAPoAABAAAQAADAAAYAACAAAIAADAAAAA==

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