3D Mol Similar

Progesterone

: Iupac Name：(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one; CAS No.: 57-83-0; Molecular Weight：314.469; Modify Date.: 2023-10-02 02:08; Introduction: Progesterone is a hormone released by luteal cells in the ovaries which contains 21 Carbon Atoms. Progesterone is also a crucial metabolic intermediate in the production of other endogenous steroids. There are two crystal forms of progesterone, that are type-α and type-β, the two types have similar physiological activity. Type-α is precipitated from dilute ethanol as orthorhombic white prismatic crystal, while type-β is orthorhombic white needle crystal, they are both insoluble in water, but soluble in ethanol, ethyl ether, chloroform, acetone, dioxane and concentrated sulfuric acid.Progesterone can be released by the ovary, placenta and adrenal cortex. Its physiological function mainly manifests in promoting estrogen treated over thicken lining of the uterus to continue the development, proliferation and thickening and hypertrophy, soften and secretion of mucus in order to make good condition for implantation of the fertilized egg. After the implantation, early stage survival and development of fertilized egg is also under the control of the high progesterone release. As a result, progesterone is a very important hormone in the female reproductive system, and it is also an important intermediate in the biosynthesis of steroid hormones. All steroid hormone releasable glands can produce progesterone, but only ovarian and placenta can release progesterone as the main hormone. Ovarian will release large amount of progesterone in the luteal phase after ovulation by granulose luteal cells, so progesterone is also named as progestin. Progesterone will decrease in result of corpus luteum atrophy. For normal women, placenta will becomes the main organ maintain progesterone after 8 to 9 weeks of pregnancy, accompany with the ovary releasing until the end of pregnancy. View more+

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1. Names and Identifiers

: 1.1 Name; Progesterone; 1.2 Synonyms; (8S,10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one (8S,9S,10R,13S,14S,17S)-17-acétyl-10,13-diméthyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-3H-cyclopenta[a]phénanthrén-3-one (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (9β,17α)-Pregn-4-ene-3,20-dione (9ξ,14ξ)-Pregn-4-ene-3,20-dione ?4-Pregnene-3,20-dione 200-350-6 4-Pregnen-3,20-dione 4-Pregnene-3,20-dione Agolutin CIDR Crinone D4-Pregnene-3,20-dione EINECS 200-350-6 Gestiron Gestron Glanducorpin Gynlutin gynoluton Gynolutone Lugesteron Lutein Luteol Luteum Lutex Lutin lutren MFCD00003658 Pregn-1-ene-3,20-dione PREGN-4-EN-3,20-DIONE Pregn-4-ene-3,20-dione Pregn-4-ene-3,20-dione, (9β,17α)- Pregn-4-ene-3,20-dione, (9ξ,14ξ)- PREGNENE-3,20-DIONE PRIMOLUT progestérone Progesterone (Prometrium) PROGESTERONE-WATER SOLUBLE progestin Progestogel Progestol Prometrium, Agolutin, Corlutin Prontogest U 3672 Vitarrine; View all

1.3 CAS No.: 57-83-0

1.4 CID: 5994

1.5 EINECS(EC#): 200-350-6

1.6 Molecular Formula: C21H30O2 (isomer)

1.7 Inchi: InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

1.8 InChIkey: RJKFOVLPORLFTN-LEKSSAKUSA-N

1.9 Canonical Smiles: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C

1.10 Isomers Smiles: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

2. Properties

2.1 Density: 1.08

2.1 Melting point: 128-132℃

2.1 Boiling point: 447.2°Cat760mmHg

2.1 Refractive index: 182 ° (C=2, Dioxane)

2.1 Flash Point: 166.7°C

2.1 Precise Quality: 314.22500

2.1 PSA: 34.14000

2.1 logP: 4.72350

2.1 Solubility: H2O: 25?mg/mL, may be clear to slightly hazy

2.2 Appearance: Crystalline Powder

2.3 Carcinogenicity: Progesterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

2.4 Chemical Properties: White powder. Melting point 121°C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.

2.5 Color/Form: Powder

2.6 Water Solubility: <0.1 g/100 mL at 19 oC

2.7 Spectral Properties: IR: 18029 (Sadtler Research Laboratories IR Grating Collection)
MASS: 1929 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 124 m/z, 272 m/z, 314 m/z

2.8 Stability: Stable. Incompatible with strong oxidizing agents.

2.9 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: progesterone: hormone, producedprimarily by the corpus luteumof the ovary but also by theplacenta, that prepares the inner liningof the uterus for implantation ofa fertilized egg cell. If implantationfails, the corpus luteum degeneratesand progesterone production ceasesaccordingly. If implantation occurs,the corpus luteum continues to secreteprogesterone, under the influenceof luteinizing hormone andprolactin, for several months of pregnancy,by which time the placentahas taken over this function. Duringpregnancy, progesterone maintainsthe constitution of the uterus andprevents further release of eggs fromthe ovary. Small amounts of progesteroneare produced by the testes.

3.2 General Description: Progesterone, pregn-4-en-3,20-dione, is so rapidly metabolized that it is not particularlyeffective orally, being only one twelfth as active as intramuscularly.An oral formulation of micronized progesterone(Prometrium) is available. Progesterone given intramuscularlycan be very irritating. A vaginal gel containing 4% or8% progesterone offers an alternative dosage form.Progesterone was originally obtained from animal ovariesbut is now prepared synthetically from plant sterol precursors.The discovery of 19-nortestosterones with progesteroneactivity made synthetically modified progestins of tremendoustherapeutic importance.Progesterone (and all other steroid 4-ene-3-ones) is lightsensitive and should be protected from light.

3.3 Purification Methods: The form crystallises from EtOH with m 127-131o. The -form crystallises from pet ether or aqueous pet ether/aqueous Et2O with m 119-120o or 121o. It also crystallises from Et2O, Me2CO/EtOAc, MeOH, aqueous Et2O, aqueous MeOH, wet pet ether, Et2O/pet ether, pet ether/*C6H6, Et2O/pentane and isopropyl ether. The is at 240nm with log 4.25 (EtOH). [Wintersteiner & Allen J Biol Chem 107 max 321 1934, Beilstein 7 III 3648, 7 IV 2395.] Progesterone Preparation Products And Raw materials Raw materials

3.4 Usage: The main physiological effects of progesterone:1. Progesterone can maintain the female animal pregnancy, and cause a series of physiological changes, such as inhibition of female estrus.2. Progesterone has the power to promote the thickening of the lining of the uterus, promote the bending of the gland and to increase secretion function.3. Progesterone can inhibit the peristalsis of the uterus, and contribute to the cervix contraction, secretion of mucus, etc.. These physiological changes provide suitable environment for the operation, growth and development of early embryos, as well as the continued growth of the fetus.4. Small amount of progesterone is also used in combination with the hormone estrogen to promote female estrus. The synergy between progesterone and prolactin can promote the development of mammary glands.5. Progesterone is involved in the feedback regulation of the hypothalamus and anterior pituitary, which makes the balance of the animal reproductive hormones. In vivo, progesterone content of all sorts of livestock follicular phase is below 1 ng/ml, while in bovine corpus luteum period is approximately 4 ng/ml, pregnancy period is about 18 ng/ml.6. Formerly biochemical study shows that progesterone modulates action as progestogens, clinical for the treatment of habitual abortion, dysmenorrhea, amenorrhea and other symptoms. One of progesterone's most important functions is as hormone drugs, to promote and maintain the uterine changes in the early stage of pregnancy, used in habitual abortion, irregular menstruation, etc.. In addition, progesterone also behaves as steroid hormone drug as well as progestogens, which is used in treatment of threatened abortion.; View all

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R40

4.1 Safety Statements: S36/37;S45

4.1 Exposure Standards and Regulations: No residues of progesterone are permitted in excess of the following increments above the concentrations of progesterone naturally present in untreated animals: In uncooked edible tissues of steers and calves: 3 ppb for muscle; 12 ppb for fat; 9 ppb for kidney; and 6 ppb for liver. In uncooked edible tissues of lambs: 3 ppb for muscle and 15 ppb for fat, kidney, and liver.
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 Octanol/Water Partition Coefficient: log Kow= 3.87

4.3 Fire Hazard: Flash point data for Progesterone are not available; however, Progesterone is probably combustible.

4.4 Hazard Declaration: H351-H361

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: UN 1648 3 / PGII

4.5 Safety Profile: NTP 10th Reporton Carcinogens. IARC Cancer Review:Animal Lirmted Evidence IMEMDT 21,491,79; Animal Sufficient EvidenceIMEMDT 6,135,74. EPA GeneticToxicology Program. Reported in EPATSCA Inventory.SAFETY PROFILE: Confirmed carcinogenwith experimental carcinogenic,neoplastigenic, tumorigenic, and teratogenicdata. Poison by intravenous andintraperitoneal routes. Human teratogeniceffects by ingestion and parenteral routes:developmental abnormalities of theurogenital system. Human malereproductive effects by intramuscular route:changes in spermatogenesis, the prostate,seminal vesicle, Cowper's gland andaccessory glands, impotence, and breastdevelopment. Human female reproductiveeffects by ingestion, parenteral, andintravaginal routes: ferthty changes;menstrual cycle changes and disorders;uterus, cervix, and vagina changes.Experimental reproductive effects. Humanmutation data reported. When heated todecomposition it emits acrid smoke andirritating fumes.

4.6 Caution Statement: P280

4.6 Formulations/Preparations: PROGESTERONE INJECTION, (PROJESTAJECT, OTHERS) CONTAINS 25 TO 100 MG PROGESTERONE PER ML OF VEGETABLE OIL. ... AQUEOUS SUSPENSIONS OF PROGESTERONE ARE PARTICULARLY PAINFUL & ARE SELDOM USED. ... PROGESTERONE IS ALSO AVAILABLE IN A T-SHAPED INTRAUTERINE CONTRACEPTIVE DEVICE THAT PROVIDES CONTINUOUS DELIVERY OF PROGESTERONE IN THE UTERINE CAVITY FOR 1 YR. THIS IS MARKETED UNDER THE NAME OF PROGESTASERT AND CONTAINS 38 MG OF PROGESTERONE.
Vials (aqueous solution and in oil), 25 mg/ml, 50 mg/ml, and 100 mg/ml. Intrauterine system, 38 mg, provides contraceptive effectiveness for a period of one year.
Grade: National Formulary
/Progesterone/ exists in two crystalline forms (alpha- and beta-) of equal physiological activity.
Alza Corp...developed and intrauterine device, Progestasert, designed to release progesterone by diffusion through a rate-controlling membrane for up to one year.

4.7 WGK Germany: 3

4.7 RTECS: TW0175000

4.7 Report: NTP 10th Report on Carcinogens. IARC Cancer Review: Animal Limited Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 491.(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) ; Animal Sufficient Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 ,1974,p. 135.(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. Reported in EPA TSCA Inventory.

4.8 Safety: Safety Information about? Progesterone (CAS NO.57-83-0):
Hazard Codes:?Xn,T
Risk Statements: 40-45?
R40: Limited evidence of a carcinogenic effect.?
R45: May cause cancer.
Safety Statements: 36/37-45-53
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S53: Avoid exposure - obtain special instructions before use.
WGK Germany: 3
RTECS: TW0175000

4.9 Specification: ?Progesterone (CAS NO.57-83-0) is also called Progestin ; Lutren ; Lutein ; Flavolutan ; Corporin ; Luteal hormone ; 4-Pregnene-3,20-dione .

4.10 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intravenous	100mg/kg (100mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968.
rat	LD50	intraperitoneal	327mg/kg (327mg/kg)	?	Drugs in Japan Vol. -, Pg. 1183, 1995.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Reproductive toxicity, Category 1A

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
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.
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

View all

6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass spectrum (electron ionization)

7. Synthesis Route

57-83-0Total: 15 Synthesis Route

57-88-5 357 Suppliers

57-83-0 489 Suppliers

145-13-1 365 Suppliers

145-15-3 13 Suppliers

Literatures:
Steroids, , vol. 31, # 3 p. 315 - 325
Yield: null

152-58-9 59 Suppliers

57-83-0 489 Suppliers

64-85-7 50 Suppliers

Literatures:
Chemical and pharmaceutical bulletin, , vol. 34, # 9 p. 3722 - 3726
Yield: ~74%

145-13-1 365 Suppliers

57-83-0 489 Suppliers

145-15-3 13 Suppliers

Literatures:
Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, , vol. 35, # 6 p. 407 - 410
Yield: null

View all

8. Other Information

8.0 Merck: 7773

8.1 BRN: 1915950

8.2 Description: Progesterone is a hormone released by luteal cells in the ovaries which contains 21 Carbon Atoms. Progesterone is also a crucial metabolic intermediate in the production of other endogenous steroids. There are two crystal forms of progesterone, that are type-α and type-β, the two types have similar physiological activity. Type-α is precipitated from dilute ethanol as orthorhombic white prismatic crystal, while type-β is orthorhombic white needle crystal, they are both insoluble in water, but soluble in ethanol, ethyl ether, chloroform, acetone, dioxane and concentrated sulfuric acid.
Progesterone can be released by the ovary, placenta and adrenal cortex. Its physiological function mainly manifests in promoting estrogen treated over thicken lining of the uterus to continue the development, proliferation and thickening and hypertrophy, soften and secretion of mucus in order to make good condition for implantation of the fertilized egg. After the implantation, early stage survival and development of fertilized egg is also under the control of the high progesterone release. As a result, progesterone is a very important hormone in the female reproductive system, and it is also an important intermediate in the biosynthesis of steroid hormones. All steroid hormone releasable glands can produce progesterone, but only ovarian and placenta can release progesterone as the main hormone. Ovarian will release large amount of progesterone in the luteal phase after ovulation by granulose luteal cells, so progesterone is also named as progestin. Progesterone will decrease in result of corpus luteum atrophy. For normal women, placenta will becomes the main organ maintain progesterone after 8 to 9 weeks of pregnancy, accompany with the ovary releasing until the end of pregnancy.; View all

8.3 Uses: The main physiological effects of progesterone:
1. Progesterone can maintain the female animal pregnancy, and cause a series of physiological changes, such as inhibition of female estrus.
2. Progesterone has the power to promote the thickening of the lining of the uterus, promote the bending of the gland and to increase secretion function.
3. Progesterone can inhibit the peristalsis of the uterus, and contribute to the cervix contraction, secretion of mucus, etc.. These physiological changes provide suitable environment for the operation, growth and development of early embryos, as well as the continued growth of the fetus.
4. Small amount of progesterone is also used in combination with the hormone estrogen to promote female estrus. The synergy between progesterone and prolactin can promote the development of mammary glands.
5. Progesterone is involved in the feedback regulation of the hypothalamus and anterior pituitary, which makes the balance of the animal reproductive hormones. In vivo, progesterone content of all sorts of livestock follicular phase is below 1 ng/ml, while in bovine corpus luteum period is approximately 4 ng/ml, pregnancy period is about 18 ng/ml.
6. Formerly biochemical study shows that progesterone modulates action as progestogens, clinical for the treatment of habitual abortion, dysmenorrhea, amenorrhea and other symptoms. One of progesterone's most important functions is as hormone drugs, to promote and maintain the uterine changes in the early stage of pregnancy, used in habitual abortion, irregular menstruation, etc.. In addition, progesterone also behaves as steroid hormone drug as well as progestogens, which is used in treatment of threatened abortion.; View all

8.4 Preparation: Progesterone can be obtained by oxidation of the pregnenolone. Dry toluene was added to a oven dried reaction kettle, and then cyclohexanone and pregnenolone were added in order with vigorous stirring to dissolve. Side product H2O was removed by Soxhlet extraction with toluene steam, aluminium isopropoxidequickly was added flowingly, the oxidation reaction was hold on at 115 oC for 2h, cooling to 80 oC, add 5% dilute sulfuric acid under stirring then stand by until water and toluene separated, the toluene layer was extracted with water to neutrality and then distillation off toluene and cyclohexanone. Cooling, filtering, filter cake was beated with petroleum, filtering, washing with petroleum, dried as crude progesterone. The crude product was dissolved in ethanol, decolorized by activated carbon, recrystallized to get the final product, yield 80%. Another way to produce progesterone is choosing the 16-Dehydropregnenolone acetate as start material, treated consecutively by catalytic hydrogenation, alkali hydrolysis, oxidation by aluminum isopropoxide, to get the progesterone as final product.; View all

8.5 Description: Progesterone, along with pregnenolone, is the biosynthetic precursor of all other steroid hormones. Progesterone is synthesized from cholesterol by the sequential action of desmolase in the mitochondria, which produces pregnenolone, followed by Δ^4,5-isomerase in the outer mitochondrial membrane and smooth endoplasmic reticulum of steroid-secreting cells. Progesterone activates the human progesterone receptor with an EC₅₀ value of 0.5 nM.

8.6 Chemical Properties: White powder. Melting point 121°C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.

8.7 Occurrence: Colchicum luteum also yields this alkaloid.

8.8 Uses: Progesterone is used as a contraceptive, for amenorrhea, for premenopausal syndrome, infertility, incomplete pregnancies, and anovulatory uterine bleeding.

8.9 Uses: Steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.This compound is a contaminant of emerging concern (CECs).

8.10 Uses: Sterid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer

8.11 Definition: progesterone: hormone, producedprimarily by the corpus luteumof the ovary but also by theplacenta, that prepares the inner liningof the uterus for implantation ofa fertilized egg cell. If implantationfails, the corpus luteum degeneratesand progesterone production ceasesaccordingly. If implantation occurs,the corpus luteum continues to secreteprogesterone, under the influenceof luteinizing hormone andprolactin, for several months of pregnancy,by which time the placentahas taken over this function. Duringpregnancy, progesterone maintainsthe constitution of the uterus andprevents further release of eggs fromthe ovary. Small amounts of progesteroneare produced by the testes.

8.12 Definition: ChEBI: A C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and ot er species.

8.13 Brand name: Crinone (Columbia); Prometrium (Unimed).

8.14 General Description: Progesterone, pregn-4-en-3,20-dione, is so rapidly metabolized that it is not particularlyeffective orally, being only one twelfth as active as intramuscularly.An oral formulation of micronized progesterone(Prometrium) is available. Progesterone given intramuscularlycan be very irritating. A vaginal gel containing 4% or8% progesterone offers an alternative dosage form.Progesterone was originally obtained from animal ovariesbut is now prepared synthetically from plant sterol precursors.The discovery of 19-nortestosterones with progesteroneactivity made synthetically modified progestins of tremendoustherapeutic importance.
Progesterone (and all other steroid 4-ene-3-ones) is lightsensitive and should be protected from light.

8.15 Air & Water Reactions: Insoluble in water.

8.16 Reactivity Profile: Progesterone is sensitive to light .

8.17 Hazard: A carcinogen (OSHA).

8.18 Health Hazard: ACUTE/CHRONIC HAZARDS: Progesterone may be absorbed through the skin.

8.19 Fire Hazard: Flash point data for Progesterone are not available; however, Progesterone is probably combustible.

8.20 Biological Activity: Endogenous progesterone receptor (PR) agonist (EC 50 = 0.5 nM).

8.21 Biochem/physiol Actions: Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

8.22 Safety Profile: NTP 10th Report on Carcinogens. IARC Cancer Review: Animal Lirmted Evidence IMEMDT 21,491,79; Animal Sufficient Evidence IMEMDT 6,135,74. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory. SAFETY PROFILE: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Poison by intravenous and intraperitoneal routes. Human teratogenic effects by ingestion and parenteral routes: developmental abnormalities of the urogenital system. Human male reproductive effects by intramuscular route: changes in spermatogenesis, the prostate, seminal vesicle, Cowper's gland and accessory glands, impotence, and breast development. Human female reproductive effects by ingestion, parenteral, and intravaginal routes: ferthty changes; menstrual cycle changes and disorders; uterus, cervix, and vagina changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

8.23 Chemical Synthesis: Progesterone, pregn-4-en-3,20-dione (28.3.1), is made by oxidizing pregnenolon with aluminum isopropylate in the presence of cyclohexanone as a proton acceptor (Oppenauer oxidation). Pregnenolon itself is made by subsequent oxidation and further cleavage of the side chain of stigmasterin, a sterin of plant origin that is isolated from soybeans.

8.24 Carcinogenicity: Progesterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

8.25 Purification Methods: The form crystallises from EtOH with m 127-131o. The -form crystallises from pet ether or aqueous pet ether/aqueous Et2O with m 119-120o or 121o. It also crystallises from Et2O, Me2CO/EtOAc, MeOH, aqueous Et2O, aqueous MeOH, wet pet ether, Et2O/pet ether, pet ether/*C6H6, Et2O/pentane and isopropyl ether. The is at 240nm with log 4.25 (EtOH). [Wintersteiner & Allen J Biol Chem 107 max 321 1934, Beilstein 7 III 3648, 7 IV 2395.]

9. Computational chemical data

Molecular Weight: 314.469g/mol
Molecular Formula: C₂₁H₃₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 314.224580195
Monoisotopic Mass: 314.224580195
Complexity: 589
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 34.1
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 6
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: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAAAAAADwSAgAACAAAAAACIAqBSAAAAAAAgAAAACAEAAEgAABIAAQAAAAAAgAAIAQMIiMCPgAAAAAAAAACAAAQAACAAAQAACAAAAA==

10. Question & Answer

What are the signs of low Progesterone in women? Apr 10 2023
Progesterone, also known as the "pregnancy hormone" or "yellow body hormone," is an important hormone naturally secreted by women, mainly produced by the ovaries. Progesterone works in conjunction wit..
What is Progesterone? Oct 12 2022
Progesterone is a type of sex hormone and a type of progestogen that is produced in the human body. In normal circumstances, the majority of progesterone in a woman's body comes from the ovaries. Duri..
What is the Role of Progesterone in the Female Reproductive System? Jun 15 2022
What is the Role of Progesterone in the Female Reproductive System? Progesterone (P4) is a steroid hormone and an intermediate of sex steroids produced by all steroidogenic tissues. It plays a crucial..
What are the effects and uses of progesterone only pills? May 29 2022
Progesterone is secreted by the corpus luteum of the ovary and has a significant morphological effect on the endometrium stimulated by estrogen in vivo, and is necessary for maintaining pregnancy. The..

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