Description Uses Preparation
ChemicalBook > CAS DataBase List > Progesterone

Progesterone

Description Uses Preparation
Product Name
Progesterone
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
Formula Weight
314.46
MOL File
57-83-0.mol
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Progesterone Property

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
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)
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Safety

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
Hazardous Substances Data
57-83-0(Hazardous Substances Data)
Toxicity
LD50 intraperitoneal in rat: 327mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H351Suspected of causing cancer

H362May cause harm to breast-fed children

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P-069
Product name
Progesterone solution
Purity
1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$142
Updated
2024/03/01
Sigma-Aldrich
Product number
BP449
Product name
Progesterone
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
50MG
Price
$233
Updated
2024/03/01
Sigma-Aldrich
Product number
5341
Product name
Progesterone - CAS 57-83-0 - Calbiochem
Purity
Steroid hormone secreted by the corpus luteum during the latter half of the menstrual cycle.
Packaging
25g
Price
$102
Updated
2024/03/01
Sigma-Aldrich
Product number
46665
Product name
Progesterone
Purity
VETRANAL
Packaging
250mg
Price
$576
Updated
2024/03/01
Sigma-Aldrich
Product number
1568007
Product name
Progesterone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$358
Updated
2024/03/01
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Progesterone Chemical Properties,Usage,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.

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.

Uses

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

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).

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.

brand name

Crinone (Columbia); Prometrium (Unimed).

Biological Functions

Progesterone is a hormone, produced primarily by the corpus luteum of the ovary but also by the placenta, that prepares the inner lining of the uterus for implantation ofa fertilized egg cell. If implantation fails, the corpus luteum degenerates and progesterone production ceases accordingly. If implantation occurs,the corpus luteum continues to secrete progesterone, under the influence of luteinizing hormone and prolactin, for several months of pregnancy,by which time the placenta has taken over this function. Duringpregnancy, progesterone maintains the constitution of the uterus and prevents further release of eggs from the ovary. Small amounts of progesterone are produced by the testes.

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).

Biochem/physiol Actions

Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

Pharmacology

During the second half of the menstrual cycle, progesterone promotes glandular growth in the endometrium, hyperemia of the uterus, thickening of the endometrium in preparation for implantation of a fertilized egg, and reduces the excitability of the uterus during pregnancy, inhibiting its activity and relaxing smooth muscles , allowing the embryo to grow safely. Under the joint action of estrogen, progesterone promotes the development of breast lobules and glands, so that the breasts can fully develop and prepare for lactation. Progesterone closes the cervix, reduces and thickens the mucus, and makes it difficult for sperm to penetrate; in large doses, it inhibits the secretion of pituitary gonadotropin through a negative feedback effect on the hypothalamus, resulting in the inhibition of ovulation. After ovulation, on the basis of the action of progesterone hormone, the endometrium continues to thicken and hyperemia, the glands proliferate and branch, from the proliferative phase to the secretory phase, which is conducive to the implantation and embryonic development of pregnant eggs. Progesterone inhibits uterine contractions and reduces the sensitivity of the uterus to oxytocin, allowing the fetus to grow safely. Progesterone competes against aldosterone, thereby promoting Na and Cl excretion and diuresis. Progesterone can slightly increase body temperature in normal women, so the basal body temperature in the luteal phase of the menstrual cycle is higher than that in the follicular phase.

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.

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.

storage

Store at RT

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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Progesterone Suppliers

Hubei Zhuxi Renfu Pharmaceutical Co., Ltd.
Tel
0719-2732885 13971206496
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market@renfu.com.cn
Country
China
ProdList
1
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Shaanxi billion Kang Long biological technology co., LTD
Tel
17791478691
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4009024560
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yklbiotech@163.com
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China
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407
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Hubei huizepu Pharmaceutical Technology Co., Ltd
Tel
0185-0185-07139096 18507139096
Fax
QQ:1925957016
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18507139096@163.com
Country
China
ProdList
3855
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Guangzhou Dreampharm Biotechnology Co., Ltd.
Tel
17825480238
Fax
QQ 3008233717
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3008233717@qq.com
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China
ProdList
9844
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Hubei widely chemical technology Co., Ltd.
Tel
027-83989310 18627915365
Fax
027-83989310
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2658488909@qq.com
Country
China
ProdList
1297
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Jiangsu Jiaerke Pharmaceuticals Group Corp., Ltd.
Tel
519-88930815 13004379774
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wu@jiaerke.com
Country
China
ProdList
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Tianmen Hengchang Chemical Co., Ltd
Tel
027-59322316 15172518801
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J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
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jkinfo@jkchemical.com
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96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
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INTATRADE GmbH
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+49 3493/605464
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+49 3493/605470
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sales@intatrade.de
Country
Germany
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3576
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View Lastest Price from Progesterone manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
Progesterone 57-83-0
Price
US $20.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-03-21
Wuhan Haorong Biotechnology Co.,Ltd
Product
Progesterone 57-83-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500
Release date
2023-07-20
Shandong Hanjiang Chemical Co., Ltd
Product
Progesterone 57-83-0
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10T
Release date
2024-01-25

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