ChemicalBook >> CAS DataBase List >>17α-Hydroxyprogesterone

17α-Hydroxyprogesterone

CAS No.
68-96-2
Chemical Name:
17α-Hydroxyprogesterone
Synonyms
17-HYDROXYPROGESTERONE;17A-HYDROXYPROGESTERONE;17α-Hydroxyprogesterone;17-OHP;prodox;HYDROXYPROGESTERONE, 17A-;prodix;U 3096;Gestageno;NSC 15468
CBNumber:
CB5181560
Molecular Formula:
C21H30O3
Molecular Weight:
330.46
MDL Number:
MFCD00003659
MOL File:
68-96-2.mol
Last updated:2024-03-22 17:12:53

17α-Hydroxyprogesterone Properties

Melting point 276°C
Boiling point 407.89°C (rough estimate)
Density 1.0998 (rough estimate)
refractive index 90 ° (C=1, CHCl3)
Flash point 9℃
storage temp. Sealed in dry,Room Temperature
solubility soluble in Chloroform
pka 13.03±0.60(Predicted)
color White to Almost white
Water Solubility 5.056mg/L(20 ºC)
Merck 14,4839
BRN 3218109
CAS DataBase Reference 68-96-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 21807M87J2
NIST Chemistry Reference Pregn-4-ene-3,20-dione, 17-hydroxy-(68-96-2)
ATC code G03DA03

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09
Signal word  Danger
Hazard statements  H360FD-H411
Precautionary statements  P202-P273-P280-P308+P313-P391-P405
Hazard Codes  T,F
Risk Statements  61-39/23/24/25-23/24/25-11
Safety Statements  53-22-36/37/39-45-36/37-16
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS  TU5060000
HS Code  38220090

17α-Hydroxyprogesterone price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H5752 17α-Hydroxyprogesterone ≥95% 68-96-2 5g $95.3 2024-03-01 Buy
Sigma-Aldrich H-085 17α-Hydroxyprogesterone solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 68-96-2 1mL $135 2024-03-01 Buy
TCI Chemical H1250 17alpha-Hydroxyprogesterone >98.0%(HPLC) 68-96-2 5g $82 2024-03-01 Buy
TCI Chemical H1250 17alpha-Hydroxyprogesterone >98.0%(HPLC) 68-96-2 25g $225 2021-12-16 Buy
Sigma-Aldrich H5752 17α-Hydroxyprogesterone ≥95% 68-96-2 25g $229.2 2024-03-01 Buy
Product number Packaging Price Buy
H5752 5g $95.3 Buy
H-085 1mL $135 Buy
H1250 5g $82 Buy
H1250 25g $225 Buy
H5752 25g $229.2 Buy

17α-Hydroxyprogesterone Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Prodox,Upjohn

Uses

17α-Hydroxy Progesterone is a metabolite of Progesterone. It was isolated from adrenal glands.

Uses

anticoagulant

Uses

Progesteron. It was isolated from adrenal glands.

Indications

Hydroxyprogesterone has been used prophylactically for the 12th to 37th week of pregnancy, particularly in women who are in the high-risk category for premature delivery (e.g., those with a history of premature delivery or spontaneous abortion). A concern relating to teratogenic potential has limited its use. Hydroxyprogesterone as a tocolytic agent requires further evaluation before its routine prophylactic administration can be recommended.

Definition

ChEBI: A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.

Manufacturing Process

A suspension of 90.0 g of δ5-pregnen-3β,17α-diol-20-one in 2300 ml of 85% formic acid was shaken for 2 h at a temperature of 70C. During this time the compound partially dissolved and at the same time a new crystalline substance appeared in the solution. After cooling, the precipitate was filtered, thus giving 80.0 g of the 3-formate of δ5-pregnen-3β,17α-diol-20-one having a melting point of 204°-207°C.
5.0 g of the 3-formate of δ5-pregnen-3β,17α-diol-20-one suspended in 120 ml of acetic anhydride was treated with 1.5 g of p-toluenesulfonic acid and the mixture was stirred for 9 h at room temperature. It was poured into water and after 2 h standing, the precipitate was filtered and washed to neutral, thus yielding the 3-formate 17-acetate of δ5-pregnen-3β,17α-diol-20-one in a yield of over 90%.
1.0 g of 3-formate 17-acetate of δ5-pregnen-3β,17α-diol-20-one was dissolved in 30 ml of xylene and 10 ml of cyclohexanone and 4 ml of the solution were distilled in order to remove traces of moisture. 1.0 g of aluminum isopropylate was added to the hot solution and the mixture was refluxed for 45 min. After cooling to 90°C, water was added and the organic solvents were removed by steam distiliation. Salt was added to the aqueous suspension and the residue was filtered, dried and extracted with hot acetone. The acetone solution was evaporated to dryness and the residue was crystallized from chloroformmethanol, thus giving 610.0 mg of the 17-acetate of δ4-pregnen-17α-ol-3,20- dione (17-acetoxy-progesterone) with a melting point of 239°-240°C.
Saponification of this compound with 1% methanolic potassium hydroxide yielded 80% of δ4-pregnen-17α-ol-3,20-dione.

Therapeutic Function

Progestin

Biological Activity

17-hydroxyprogesterone, an endogenous progestogen and chemical intermediate in the biosynthesis of other steroid hormones, is also the parent compound of various progestins derivatives.

Synthesis

Hydroxyprogesterone, 17|á-hydroxypregn-4-en-3,20-dione (28.3.6), is synthesized from dehydropregnenolon (28.3.2). Dehydropregnenolon itself is made by successive decomposition and oxidation of the side spiroketal group of diosgenin?athe aglycone of one of the saponins of plant origin isolated from Discorea. The double bond at C16¨CC17 or dehydropregnenolon is oxidized by hydrogen peroxide in the presence of a base to give an epoxide (28.3.3). Interaction of the resulting epoxide with hydrogen bromide in acetic acid forms a bromohydrin (28.3.4). The hydroxyl group of C3 of the steroid system is formylated by formic acid, and reduction by hydrogen over a palladium catalyst removes the bromine atom at C16, forming the product (28.3.5). The hydroxyl group at C17 of this product is acylated by acetic acid anhydride and then the formyl group at C3 is oxidized by aluminum isopropylate in the presence of cyclohexanone, during which simultaneous isomerization takes place at the double bond, isomerizes from C5¨CC6 to position C4¨CC5, forming the desired hydroprogesterone ester, in the given case an acetate (28.3.6), in which form it is used in medical practice. Other alternative ways of synthesis have been proposed.

Synthesis_68-96-2

in vitro

17-hydroxyprogesterone was found to be an agonist of the progesterone receptor (pr), which was similarly to progesterone. in addition, 17-hydroxyprogesterone was also an antagonist of the mineralocorticoid receptor (mr) as well as a partial agonist of the glucocorticoid receptor (gr), with very low potency (ec50>100-fold less relative to cortisol), which was also similarly to progesterone [1].

in vivo

findings from a previous rat in vivo study demonstrated that even if modest, lowering blood pressure with 17-hydroxyprogesterone could be a viable treatment selection for blocking inflammation and uterine artery vasoconstriction, whereas improving litter size [2].

References

[1] barbara j. attardi, et al. comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate (17-ohpc), and related progestins. am j obstet gynecol. 2007 dec; 197(6): 599.e1–599.e7.
[2] lorena m. amaral, et al. 17- hydroxyprogesterone caproate significantly improves clinical characteristics of preeclampsia in the rupp rat model. hypertension. 2015 jan; 65(1): 225–231.
[3] ryckman kk,cook de,berberich sl,shchelochkov oa,berends sk,busch t,dagle jm,murray jc. replication of clinical associations with 17-hydroxyprogesterone in preterm newborns. j pediatr endocrinol metab. 2012;25(3-4):301-5.

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View Lastest Price from 17α-Hydroxyprogesterone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
17-alpha-hydroxyprogesterone pictures 2024-03-28 17-alpha-hydroxyprogesterone
68-96-2
US $0.00 / kg 1kg 0.99 10T Shandong Hanjiang Chemical Co., Ltd
17α-hydroxyprogesterone pictures 2024-03-28 17α-hydroxyprogesterone
68-96-2
US $90.00-80.00 / kg 0.10000000149011612kg min99% 100 tons Hebei Kangcang new material Technology Co., LTD
Hydroxyprogesterone pictures 2024-03-28 Hydroxyprogesterone
68-96-2
US $200.00-100.00 / g 1g 98% 20 Hebei Kangcang new material Technology Co., LTD
  • Hydroxyprogesterone pictures
  • Hydroxyprogesterone
    68-96-2
  • US $200.00-100.00 / g
  • 98%
  • Hebei Kangcang new material Technology Co., LTD
17-Hydroxypregn-4-en-3,20-dione 17-hydroxy-pregn-4-ene-20-dione 17-hydroxypregn-4-ene-3,20-dione delta(4)-pregnene-17alpha-ol-3,20-dione gestagenogador prodix (8R,9S,10R,13S,14S,17R)-17-ACETYL-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE 4-PREGNEN-17ALPHA-OL-3,20-DIONE 4-pregnen-17a-ol-3,20-dione 4-PREGNEN-17-OL-3,20-DIONE 17a-hydroxypregn-4-ene-3,20-dione 17A-HYDROXY-4-PREGNENE-3,20-DIONE 17ALPHA-HYDROXY-4-PREGNENE-3,20-DIONE 17alpha-Hyroxyprogesterone 17alpha-Hydroxypregn-4-Ene-3,20-Dione Acetate 17A-HYDROXYPROGESTERON VETRANAL, 250 MG 17-Hydroxy Pregn-4-ene-3,20-dione, 17-hydroxy- 17α-hydroxy-4-pregnene-3,20-dione 17-HYDROXYPROGESTERONE ACETATE & BASE HYDROXYPROGESTERONE (8R,9S,10R,13S,14S,17R)-17-ACETYL-17-HYDROXY-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15 (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-diMethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one Hydroxyprogesterone 17a-Hydroxyprogesterone 17α-Hydroxyprogesterone solution 17alpha-Hydroxyprogesterone solution, 100ppm 17α-Hydroxy-4-pregnene-3,20-dione, 4-Pregnen-17α-ol-3,20-dione Gestageno (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one (8R,9S,10R,13S,14S,17R)-17-ethanoyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one 17α-Hydroxyprogesterone,17α-Hydroxy-4-pregnene-3,20-dione, 4-Pregnen-17α-ol-3,20-dione 17α-Hydroxylutin 17α-Hydroxy-P4 NSC 15468 Pregn-4-en-17α-ol-3,20-dione U 3096 17α-Hydroxyprogesterone> Progesterone 17-Hydroxy Impurity 4-Pregnen-17α-ol-3,20-dione-d8 17α-Hydroxyprogesterone Solution Hydroxyprogesterone USP/EP/BP ydroxyprogesterone Progesterone 17α-Hydroxy Impurity 17α-Hydroxy ProgesteroneQ: What is 17α-Hydroxy Progesterone Q: What is the CAS Number of 17α-Hydroxy Progesterone Q: What is the storage condition of 17α-Hydroxy Progesterone Q: What are the applications of 17α-Hydroxy Progesterone 17a-Hydroxy Progesterone API AI3-26538 prodox 17A-HYDROXYPROGESTERONE 17-HYDROXYPROGESTERONE HYDROXYPROGESTERONE, 17A- 17-OHP 17α-Hydroxyprogesterone 17alpha-Hydroxyprogesterone 17alpha-Hydoxyprogesterone 17alpha-Hydroxyprogesteron 17a-hydyoxyprogesterone 17-ALPHA-HYDROXYPREGN-4-ENE-3,20-DIONE 17ALPHA-HYDROXY-4-PREGNENE-3,20-DIONE