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Progesterone

Description Uses Preparation
Progesterone
Progesterone structure
CAS No.
57-83-0
Chemical Name:
Progesterone
Synonyms
CIDR;Prog;Lutex;Lutin;Luteol;U 3672;Lutein;lutren;Luteum;Luteine
CBNumber:
CB4224484
Molecular Formula:
C21H30O2
Formula Weight:
314.46
MOL File:
57-83-0.mol

Progesterone Properties

Melting point:
128-132 °C (lit.)
alpha 
186 º (c=1, ethanol)
Boiling point:
394.13°C (rough estimate)
Density 
d23 1.166; d20 1.171
refractive index 
182 ° (C=2, Dioxane)
Flash point:
2℃
storage temp. 
room temp
solubility 
H2O: 25 mg/mL, may be clear to slightly hazy
form 
powder
color 
Yellow to yellow-brown
Water Solubility 
<0.1 g/100 mL at 19 ºC
Merck 
7773
BRN 
1915950
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
RJKFOVLPORLFTN-LEKSSAKUSA-N
CAS DataBase Reference
57-83-0(CAS DataBase Reference)
FDA 21 CFR
556.540
EWG's Food Scores
4-7
FDA UNII
4G7DS2Q64Y
NCI Dictionary of Cancer Terms
progesterone; progestin
NCI Drug Dictionary
Lutex
ATC code
G03DA04
Proposition 65 List
Progesterone
NIST Chemistry Reference
Progesterone(57-83-0)
EPA Substance Registry System
Progesterone (57-83-0)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08,GHS02,GHS07
Signal word  Danger
Hazard statements  H225-H302+H312+H332-H319-H351-H360
Precautionary statements  P201-P308+P313-P210-P261-P280-P305+P351+P338-P370+P378-P403+P235
Hazard Codes  Xn,T,F
Risk Statements  40-45-62-36-20/21/22-11
Safety Statements  36/37-45-53-16
RIDADR  UN 1648 3 / PGII
WGK Germany  3
RTECS  TW0175000
HS Code  29372390
Toxicity LD50 intraperitoneal in rat: 327mg/kg
NFPA 704
1
1 1

Progesterone price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 5341 Progesterone - CAS 57-83-0 - Calbiochem Steroid hormone secreted by the corpus luteum during the latter half of the menstrual cycle. 57-83-0 25 g $74.92 2021-03-22 Buy
Sigma-Aldrich P-069 Progesterone solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? 57-83-0 1 mL $112 2021-03-22 Buy
Sigma-Aldrich BP449 Progesterone British Pharmacopoeia (BP) Reference Standard 57-83-0 $190 2021-03-22 Buy
Sigma-Aldrich P3300000 Progesterone European Pharmacopoeia (EP) Reference Standard 57-83-0 $190 2021-03-22 Buy
Sigma-Aldrich Y0001665 Progesterone for system suitability European Pharmacopoeia (EP) Reference Standard 57-83-0 $190 2021-03-22 Buy

Progesterone Chemical Properties,Uses,Production

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.

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.

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.

Chemical Properties

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

Occurrence

Colchicum luteum also yields this alkaloid.

Uses

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

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

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.

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.

brand name

Crinone (Columbia); Prometrium (Unimed).

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Progesterone is sensitive to light .

Hazard

A carcinogen (OSHA).

Health Hazard

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

Fire Hazard

Flash point data for Progesterone are not available; however, Progesterone is probably combustible.

Biological Activity

Endogenous progesterone receptor (PR) agonist (EC 50 = 0.5 nM).

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.

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.

Carcinogenicity

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

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

Preparation Products


Progesterone Suppliers

Global( 612)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
HANGZHOU CLAP TECHNOLOGY CO.,LTD
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View Lastest Price from Progesterone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-08 Gynolutone
57-83-0
US $30.00 / KG 1KG 99.9% 1000kg/month Shanxi Lianxu New Material Co., LTD
2021-12-08 Progesterone
57-83-0
US $74.00 / g 10g 99% 1000kg/month Shanxi Lianxu New Material Co., LTD
2021-12-08 Progesterone
57-83-0
US $10.00 / KG/Tin 1KG 99% 10Tons Isonicotinic acid Hebei Senko Biotechnology Co., Ltd.

Progesterone Spectrum


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