Hydroxyprogesterone

Iupac Name：(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

CAS No.: 68-96-2

Molecular Weight：330.468

Modify Date.: 2022-11-07 06:39

Introduction: 17α-Hydroxy Progesterone is a metabolite of Progesterone. It was isolated from adrenal glands. View more+

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1. Names and Identifiers

1.1 Name: Hydroxyprogesterone
1.2 Synonyms: (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 17a-Hydroxypregn-4-ene-3,20-dione 17A-hydroxyprogesterone 17alpha-hydroxyprogesterone 17-Hydroxypregn-4-en-3,20-dione 17-hydroxy-pregn-4-ene-20-dione 17-hydroxypregn-4-ene-3,20-dione 17-Hydroxyprogesterone 17α-Hydroxypregn-4-ene-3,20-dione 17α-Hydroxyprogesterone 4-Pregnen-17a-ol-3,20-dione 4-Pregnen-17α-ol-3,20-dione delta(4)-pregnene-17alpha-ol-3,20-dione EINECS 200-699-4 Gestageno gestagenogador hydroxyprogesteronum [INN_la] L E5 B666 OV MUTJ A1 E1 FV1 FQ &&17α MFCD00003659 Pregn-4-ene-3,20-dione, 17-hydroxy- prodix prodox

1.3 CAS No.: 68-96-2

1.4 CID: 6238

1.5 EINECS(EC#): 200-699-4

1.6 Molecular Formula: C21H30O3 (isomer)

1.7 Inchi: InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

1.8 InChkey: DBPWSSGDRRHUNT-CEGNMAFCSA-N

1.9 Canonical Smiles: CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O

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

2. Properties

2.1 Density: 1.15

2.1 Melting point: 276℃

2.1 Boiling point: 482.9 °C at 760 mmHg

2.1 Refractive index: 90 ° (C=1, CHCl3)

2.1 Flash Point: 259.9 °C

2.1 Precise Quality: 330.21900

2.1 PSA: 54.37000

2.1 logP: 3.69430

2.1 Solubility: 5.056mg/L(20 ºC)

2.2 Appearance: White solid

2.3 Chemical Properties: White Solid

2.4 Color/Form: Powder

2.5 Physical: Solid

2.6 pKa: 13.03±0.60(Predicted)

2.7 Water Solubility: 5.056mg/L(20 ºC)

2.8 Spectral Properties: SPECIFIC OPTICAL ROTATION (CHLOROFORM, 1.0417%): +105.6 DEG @ 17 DEG C/D

2.9 Stability: CRYSTALS SHOULD NOT BE EXPOSED TO HEAT & LIGHT /CAPROATE;/

2.10 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

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

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 26 companies from 3 notifications to the ECHA C&L Inventory.

H360 (92.31%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501

3.3 Methods of Manufacturing: HYDROXYPROGESTERONE; IS ESTERIFIED BY HEATING WITH CAPROIC ANHYDRIDE; IN PRESENCE OF P-TOLUENE-SULFONIC ACID; UNDER ATMOSPHERE OF NITROGEN;. US PATENT 2,753,360. /CAPROATE;/

3.4 Usage: Progesteron. It was isolated from adrenal glands.

4. Safety and Handling

4.1 Symbol: GHS02, GHS06, GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: 61

4.1 Safety Statements: 53-22-36/37/39-45

4.1 Hazard Declaration: H225-H301 + H311 + H331-H370

4.1 RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution

4.1 Caution Statement: P210-P260-P280-P301 + P310-P311

4.1 Formulations/Preparations: HYDROXYPROGESTERONE CAPROATE INJECTION, USP (DELALUTIN), IS PROVIDED AS OILY SOLN OF 125 MG/ML (IN SESAME OIL) OR 250 MG/ML (IN CASTOR OIL) FOR IM INJECTION. /CAPROATE/

4.2 WGK Germany: 3

4.2 RTECS: TU5060000

4.2 Safety: Hazard Codes:T
Risk Statements:61
61:May cause harm to the unborn child
Safety Statements:53-22-36/37/39-45
53:Avoid exposure - obtain special instruction before use
22:Do not breathe dust
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
WGK Germany:3

4.3 Specification: White Solid
usageEng:Progesteron. It was isolated from adrenal glands.
Safety Statements:53-22-36/37/39-45
53:Avoid exposure - obtain special instruction before use
22:Do not breathe dust
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	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

Mass spectrum (electron ionization)

7. Synthesis Route

68-96-2Total: 44 Synthesis Route

63-05-8 201 Suppliers

68-96-2 219 Suppliers

Literatures:
Bulletin of the Chemical Society of Japan, , vol. 58, # 3 p. 978 - 980
Yield: null

57-83-0 487 Suppliers

68-96-2 219 Suppliers

Literatures:
ChemBioChem, , vol. 12, # 17 p. 2537 - 2539
Yield: null

57-83-0 487 Suppliers

68-96-2 219 Suppliers

1045-69-8 369 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 114, # 21 p. 8309 - 8310
Yield: null

View all

8. Precursor and Product

precursor:

82427-84-7

28439-56-7

387-79-1

152-58-9

63-05-8

4470-79-5

20380-16-9

57-83-0

1097-51-4

1048-89-1

83914-30-1

570-59-2

4134-58-1

145-13-1

View all

product :

3386-00-3

1882-82-2

64-85-7

152-58-9

63-05-8

50-23-7

641-77-0

2381-45-5

808-48-0

972-46-3

9. Other Information

9.0 Merck: 14,4839

9.1 Chemical Properties: White Solid

9.2 Uses: Progesteron. It was isolated from adrenal glands.

9.3 Uses: anticoagulant

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

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

9.6 BRN: 3218109

9.7 Originator: Prodox,Upjohn

9.8 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.

9.9 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.

9.10 Therapeutic Function: Progestin

9.11 Chemical Synthesis: Hydroxyprogesterone, 17α-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—the aglycone of one of the saponins of plant origin isolated from Discorea. The double bond at C16–C17 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–C6 to position C4–C5, 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.

10. Computational chemical data

Molecular Weight: 330.468g/mol
Molecular Formula: C₂₁H₃₀O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 330.21949481
Monoisotopic Mass: 330.21949481
Complexity: 635
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 54.4
Heavy Atom Count: 24
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: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAACAAAD0SAgAACAAAAAgCIAqBSAAIAAAAgAAAACAFAAEgAABIAAQAAQAAEgAAIAQOIyPCPgAAAAAAAAACAAAQAACAAAYAADAAAAA==

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