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Progesterone

Progesterone Structure
CAS No.
57-83-0
Chemical Name:
Progesterone
Synonyms
Lutein;PROCYANIDINS;Progesteron;Progestrone;Lutin;progestin;Luteine;Prometrium;Pregn-4-ene-3,20-dione;CIDR
CBNumber:
CB4224484
Molecular Formula:
C21H30O2
Molecular Weight:
314.46
MOL File:
57-83-0.mol
MSDS File:
SDS
Modify Date:
2024/6/25 9:40:26

Progesterone Properties

Melting point 128-132 °C (lit.)
Boiling point 394.13°C (rough estimate)
alpha 186 º (c=1, ethanol)
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
BCS Class 4
Stability Stable. Incompatible with strong oxidizing agents.
InChIKey RJKFOVLPORLFTN-LEKSSAKUSA-N
LogP 3.870
CAS DataBase Reference 57-83-0(CAS DataBase Reference)
NIST Chemistry Reference Progesterone(57-83-0)
EPA Substance Registry System Progesterone (57-83-0)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Danger
Hazard statements  H351-H360FD-H362
Precautionary statements  P202-P260-P263-P264-P270-P308+P313
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(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) P8783 Progesterone powder, BioReagent, suitable for cell culture 57-83-0 1G ₹2792.85 2022-06-14 Buy
Sigma-Aldrich(India) V900699 Progesterone Vetec?, reagent grade, 98% 57-83-0 5G ₹4124.33 2022-06-14 Buy
Sigma-Aldrich(India) P8783 Progesterone powder, BioReagent, suitable for cell culture 57-83-0 5G ₹5693.95 2022-06-14 Buy
Sigma-Aldrich(India) PHR1142 Progesterone Pharmaceutical Secondary Standard; Certified Reference Material 57-83-0 1G ₹8270.3 2022-06-14 Buy
Sigma-Aldrich(India) P8783 Progesterone powder, BioReagent, suitable for cell culture 57-83-0 25G ₹18694.78 2022-06-14 Buy
Product number Packaging Price Buy
P8783 1G ₹2792.85 Buy
V900699 5G ₹4124.33 Buy
P8783 5G ₹5693.95 Buy
PHR1142 1G ₹8270.3 Buy
P8783 25G ₹18694.78 Buy

Progesterone Chemical Properties,Uses,Production

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 Δ4,5-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.

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.

Definition

ChEBI: Progesterone is 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 other species. It has a role as a contraceptive drug, a progestin, a progesterone receptor agonist, a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.

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).

Side effects

Common side effects of oral Progesterone include: chest pain, chills, cold or flu-like symptoms; cough or hoarseness; fever, and problems with urination. Rare side effects include: clear or bloody discharge; dimpling of the breast skin, lumps in the breast or armpit; persistent crusting or flaking; redness or swelling of the breast; and sores on the breast skin that do not heal. Other side effects that may occur are: abdominal or stomach pain; constipation, difficulty breathing, dizziness, fast, strong, or irregular heartbeat or pulse; headache, measles, indigestion, itching, joint pain, stiffness, or swelling; rash.

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.

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.]

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