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Estrone(CAS No. 53-16-7)

Estrone C18H22O2 (cas 53-16-7) Molecular Structure

53-16-7 Structure

Identification and Related Records

【Name】
Estrone
【CAS Registry number】
53-16-7
【Synonyms】
delta-1,3,5-estratrien-3-beta-ol-17-one
Hormestrin
Oestrin
delta-1,3,5-oestratrien-3-beta-ol-17-one
Estrona [Spanish]
CMC_13458
Ovifollin
Wynestron
component of Mal-O-Fem
Cristallovar
Menagen
Estrusol
hydroxyestrones
Ketohydroxyoestrin
.delta.-1,3, 5-Oestratrien-3.beta.-ol-17-one
Folipex
3-Hydroxy-17-keto-estra-1,3,5-triene
Disynformon
3-Hydroxy-oestra-1,3, 5(10)-trien-17-one
Estrone-A
Destrone
Ovex (tablets)
Estrol
Follicunodis
【EINECS(EC#)】
200-164-5
【Molecular Formula】
C18H22O2 (Products with the same molecular formula)
【Molecular Weight】
270.37
【Inchi】
InChI=1/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
【InChIKey】
DNXHEGUUPJUMQT-UHFFFAOYSA-N
【Canonical SMILES】
CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
【Isomers smiles】
C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
【MOL File】
53-16-7.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.164 g/cm3
【Melting Point】
258-261℃
【Boiling Point】
445.2 oC at 760 mmHg
【Refractive Index】
165 ° (C=1, Dioxane)
【Flash Point】
189.7 oC
【Alpha】
158 o (C=1, DIOXANE)
【Water】
0.03 g/L
【Solubilities】
0.03 g/L
【Color/Form】
Small, white crystals, or white to creamy white, crystalline powder.
ALPHA: MONOCLINIC CRYSTALS FROM ALC; BETA & GAMMA: ORTHORHOMBIC CRYSTALS FROM ALC
Crystals from acetone
Exists in three crystalline phases, one monoclinic, the other two orthorhombic.
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29335995
【Storage temp】
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.
【Spectral properties】
SPECIFIC OPTICAL ROTATION: +158 TO +165 DEG @ 25 DEG C/D (DIOXANE)
Specific optical rotation: +152 deg @ 22 deg C/D (concentration by volume = 0.995 g in 100 ml chloroform)
SADTLER REF NUMBER: 1288 (IR, PRISM); MAX ABSORPTION (ALC): 280 NM (LOG E= 3.37)
IR: 5481 (Coblentz Society Spectral Collection)
UV: 20783 (Sadtler Research Laboratories Spectral Collection)
MASS: 1958 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Maximum absorption (p-dioxane): 282, 296 nm (E 2300, 2130); (concentrated sulfuric acid): 300, 450 nm; (0.1M sodium hydroxide): 239, 293 nm
【Computed Properties】
Molecular Weight:270.36608 [g/mol]
Molecular Formula:C18H22O2
XLogP3:3.1
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:18
Exact Mass:270.16198
MonoIsotopic Mass:270.16198
Topological Polar Surface Area:37.3
Heavy Atom Count:20
Formal Charge:0
Complexity:418
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:4
Effective Rotor Count:1.2
Conformer Sampling RMSD:0.6
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R45;R60;R61
【Safety Statements 】
S53;S45
【HazardClass】
3
【Safety】

Hazard Codes of Estrone (CAS NO.53-16-7):?T
Risk Statements: 45-60-61?
R45: May cause cancer.?
R60: May impair fertility.?
R61: May cause harm to the unborn child.
Safety Statements: 53-45?
S53: Avoid exposure - obtain special instructions before use.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: KG8575000
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A poison by intraperitoneal and subcutaneous routes. Human reproductive effects by implantation: spermatogenesis and impotence. Mutation data reported. A steroid drug for the treatment of menopause and ovariectomy symptoms. When heated to decomposition it emits acrid smoke and irritating fumes.

【PackingGroup 】
I; II; III
【Formulations/Preparations】
GRADES: NF
VARIOUS SULFATE ESTERS OF ESTRONE, NF ... AVAILABLE IN TABLETS CONTAINING 0.75 TO 5 MG (MORESTIN, OGEN) ... THESE ESTERS & ESTRONE ... ALSO SUPPLIED UNDER VARIOUS TRADE NAMES IN AQUEOUS SUSPENSION & OILY SOLN CONTAINING 1 TO 5 MG/ML FOR IM INJECTION.
Parenteral suspension: 5 mg/ml
Vials, 2 mg/ml and 5 mg/ml.
【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).
【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/
HERMETICALLY SEALED MACHINES, DUST ASPIRATION & AIR CONDITIONING ARE IMPORTANT SAFETY MEASURES.
【Specification】

Synonyms of?Estrone (CAS NO.53-16-7) are1,3,5(10)-Estratrien-3-ol-17-one ;?1,3,5(10)-Oestratrien-3-ol-17-one ;?3-08-00-01171 (Beilstein Handbook Reference) ;?3-Hydroxy-17-keto-estra-1,3,5-triene ;?3-Hydroxy-17-keto-oestra-1,3,5-triene ;?3-Hydroxy-oestra-1,3,5(10)-trien-17-one ;?3-Hydroxyestra-1,3,5(10)-trien-17-one ;?3-Hydroxyestra-1,3,5(10)-triene-17-one ;?Aquacrine ;?Crinovaryl ;?Cristallovar ;?Crystogen ;?Destrone ;?Disynformon ;?E(sub 1) ;?Endofolliculina ;?Estra-1,3,5(10)-trien-17-one, 3-hydroxy- ;?Estrogenic substance ;?Estron ;?Estrona ;?Estrone-A ;?Estronum ;??Estrovarin ;?Estrugenone ;?Estrusol ;?Fem-O-Gen ;?Femestrone injection ;?Femidyn ;?Folikrin ;?Folipex ;?Folisan ;?Follestrine ;?Follestrol ;?Follicular hormone ;?Folliculin ;?Folliculine ;?Folliculine benzoate ;?Follicunodis ;?Glandubolin ;?Hiestrone ;?Hormestrin ;?Hormofollin ;?Hormovarine ;?Kestrone ;?Ketodestrin ;?Ketohydroxy-estratriene ;?Ketohydroxyestrin ;?Ketohydroxyoestrin ;?Kolpon ;?Menagen ;?Menformon ;?Mestronaq ;?Natural estrogenic substance-estrone ;?Oestrin ;?Oestroform ;?Oestrone ;?Oestronum ;?Oestroperos ;?Ovex (tablets) ;?Ovifollin ;?Perlatan ;?Solliculin ;?Theelin ;?Thelestrin ;?Thelykinin ;?Thynestron ;?Tokokin ;?Unden ;?Unden (pharmaceutical) ;?Wynestron ;?delta-1,3,5-Estratrien 3beta-ol-17-one ;?delta-1,3,5-Oestratrien-3beta-ol-17-one ;?delta-1,3,5-estratrien-3-beta-ol-17-one ;?delta-1,3,5-oestratrien-3-beta-ol-17-one .

【Octanol/Water Partition Coefficient】
log Kow= 3.13
【Report】

NTP 10th Report on Carcinogens. Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 123.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?)IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 343.(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) . Reported in EPA TSCA Inventory.

【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... FROM MEXICAN YAM ... VIA 16-DEHYDROPREGNENOLONE ACETATE ... SIDE CHAIN @ POSITION-17 ... DEGRADED BY ... FORMING 2-OXIME & THEN ... BECKMANN REARRANGEMENT WITH P-ACETAMIDOBENZENESULFONYL CHLORIDE TO 17-ACETAMIDO ... WHICH ... WITH ... SULFURIC ... FORMS ENAMINE ACETATE ... HYDROLYZED TO ... ESTRONE.
Isolated from pregnant human urine, synthesis from ergosterol.
Occurs in pregnancy urine on women and mares, in follicular liquor of many animals, in human placenta, in urine of bulls and stallions, in palm-kernel oil. Isoln: Butenandt, Naturwiss. 17, 879 (1929); Doisy et al., Am. J. Physiol. 90, 329 (1929).
Also isolated from moghat roots and date palm pollen grains: Amin et al., Phytochemistry 8, 295 (1969).
Estrone is synthesized from androstenolone, which is first hydrogenated with palladium charcoal to give epiandro sterone...
【Usage】

A metabolite of 17-Estradiol

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds.
【Therapeutic Uses】
Estrogens may be effective in the prevention of cardiovascular disease in postmenopausal women. /Estrogens; NOT included in US product labeling/
Estrone ... /is/ indicated to replace estrogen in the treatment of atrophic vaginitis, vulvar atrophy (also called kraurosis vulvae), and moderate to severe vasomotor symptoms associated with menopause. ... /Included in US product labeling/
Estrone ... /is/ indicated to replace estrogen in the treatment of female hypogonadism, primary ovarian failure, or ovariectomy. ... /Included in US product labeling/
Estrone ... /is/ indicated for treatment of advanced prostatic carcinoma. /Included in US product labeling/
Estrone /is/ indicated in the treatment of abnormal uterine bleeding associated with a hypoplastic or atrophic endometrium without organic pathology. Continuous treatment with estrogen without a progestin may cause abnormal uterine bleeding with or without organic pathology. /Included in US product labeling/
OSTEOPOROSIS ... SENILE OSTEOPOROSIS ... /&/ ... POSTMENOPAUSAL OSTEOPOROSIS. ... AFTER SEVERAL MO OF ESTROGEN REPLACEMENT IN POSTMENOPAUSAL PATIENTS, CALCIUM BALANCE BECOMES POSITIVE & BONE RESORPTION DECR TO NORMAL, AND INCIDENCE OF HIP FRACTURES IS DECR. /ESTROGENS/
MAJOR USE OF ESTROGENS IS IN COMBINATION WITH PROGESTINS AS ORAL CONTRACEPTIVES. ... TREATMENT /DURING &/OR FOR MENOPAUSE/ WITH ESTROGEN IS SPECIFIC & EFFECTIVE. ... SENILE OR ATROPHIC VAGINITIS, OFTEN ASSOC WITH CHRONIC INFECTION OF ATROPHIC STRUCTURES, RESPONDS WELL TO ESTROGEN. /ESTROGENS/
Dysmenorrhea can be relieved by inhibition of ovulation with estrogen. ... Although estrogen can be used with some success /in endometriosis/, the cyclic use of a progestin is logically preferred. /Estrogen/
The common form of acne is a feature of puberty in both sexes, and androgens seem to be the essential factor, operating through stimulation of sebaceous glands. Treatment with estrogen is effective in both sexes by suppressing gonadotropins and gonadal androgen secretion, but its usefulness in the male is obviously limited. /Estrogen/
INTRAMUSCULAR: ... FOR DYSFUNCTIONAL UTERINE BLEEDING, ... SEVERAL DAYS UNTIL BLEEDING ... CONTROLLED, FOLLOWED BY ADMIN OF PROGESTAGEN FOR ONE WEEK. /ESTROGENS/
FOR PROSTATIC CARCINOMA /ESTROGENS/
Estrogen indicated for im use for moderate to severe vasomotor symptoms associated with the menopause, atrophic vaginitis, kraurosis vulvae, female hypogonadism, female castration, and primary ovarian failure.
MEDICATION (VET): estrogenic hormone therapy.
ESTROGENS ARE LARGELY RESPONSIBLE FOR CHANGES THAT TAKE PLACE @ PUBERTY IN GIRLS, AND THEY GO A LONG WAY TOWARD ACCOUNTING FOR THE ATTRIBUTES OF FEMININITY. BY A DIRECT ACTION, THEY CAUSE GROWTH & DEVELOPMENT OF VAGINA, UTERUS, & FOLLOPIAN TUBES. /ESTROGENS/
Alteration of the hormonal environment can be used as a palliative measure in the therapy of metastatic breast cancer. ... Administration of estogens can prolong both the quality and the duration of life. Favorable responses can be obtained in about 60 to 70% of patients if estrogen or progesterone receptors are present in the tumor, while such responses are observed in only 10 to 20% if receptors are absent. /Estrogen/
Since the prostate is a target organ for the actions of androgens, the inhibition of androgen secretion can be used as palliative therapy in patients with metastatic prostatic carcinoma. This can be accomplished by orchiectomy and/or the administration of an estrogen such as diethylstilbestrol. /Estrogen/
Conjugated estrogens have been used to induce ovulation in anovulatory women. They have also been used as partially sucessful contraceptives when given within 72 hours of unprotected, midcycle coitus. /Estrogens, conjugated/
【Biomedical Effects and Toxicity】
Estrogens are available for oral, parenteral, transdermal, or topical administration ... absorption is generally good withthe appropriate preparation. /Estrogens/
URINARY EXCRETION RATE OF ESTROGENS IS QUITE SIMILAR WHETHER AGENTS ARE GIVEN ORALLY OR IV, WHICH SUGGESTS THAT ABSORPTION ... FROM GI TRACT IS PROMPT & QUITE COMPLETE. /ESTROGENS/
LIMITED ORAL EFFECTIVENESS OF NATURAL ESTROGENS & THEIR ESTERS IS ... DUE TO HEPATIC METABOLISM. ESTROGENS ... WHEN DISSOLVED IN OIL AND INJECTED, ... ARE RAPIDLY ABSORBED & QUICKLY METABOLIZED. /ESTROGENS/
ESTROGENS & THEIR ESTERS ARE HANDLED IN BODY IN MUCH THE SAME WAY AS ARE ENDOGENOUS HORMONES. INACTIVATION OF ESTROGEN IS CARRIED OUT MAINLY IN LIVER. CERTAIN PROPORTION ... IS EXCRETED INTO BILE, AND THEN REABSORBED FROM INTESTINE. /ESTROGENS/
NATURAL ESTROGENS CIRCULATE IN BLOOD IN ASSOC WITH PROTEINS, INCL SEX HORMONE-BINDING GLOBULIN AND ALBUMIN. A SIGNIFICANT PROPORTION ... IS IN FORM OF CONJUGATES, PARTICULARLY SULFATE, WHICH ARE EXCRETED BY THE KIDNEY. /ESTROGENS/
Distribution: To most tissues, especially breast, uterine, vaginal, hypothalamic, and pituitary tissues; high affinity for adipose tissue. /Estrogens/
Protein binding: Moderate to high (50 to 80% to albumin and sex hormone binding globulin. /Estrogens/
Elimination: Primarily renal excretion of metabolites, some fecal; undergo extensive enterohepatic recirculation. Prolonged in obese patients. /Estrogens/
Estrogens are excreted in milk. Potential for decreased milk volume and decreased nitrogen and protein content; ... /Estradiol; from table/

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