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630-56-8

Basic Information
CAS No.: 630-56-8
Name: Hydroxyprogesterone caproate
Molecular Structure:
Molecular Structure of 630-56-8 (Hydroxyprogesterone caproate)
Formula: C27H40O4
Molecular Weight: 428.67
Synonyms: Pregn-4-ene-3,20-dione,17-hydroxy-, hexanoate (7CI,8CI);Progesterone, 17-hydroxy-, hexanoate (6CI);Hexanoic acid, ester with 17-hydroxypregn-4-ene-3,20-dione (8CI);17a-Caproyloxypregn-4-ene-3,20-dione;17a-Hydroxypregn-4-ene-3,20-dionecaproate;17a-Hydroxypregn-4-ene-3,20-dionehexanoate;17a-Hydroxyprogesteronecaproate;17a-Hydroxyprogesteronen-caproate;Delalutin;Depo-proluton;Hormofort;Pregn-4-ene-3,20-dione,17-[(1-oxohexyl)oxy]-;NSC 17592;Neolutin;Primolut Depot;Procyte Depo;Proge;Syngynon;Teralutil;
EINECS: 211-138-8
Density: 1.1 g/cm3
Melting Point: 119 °C
Boiling Point: 536.4 °C at 760 mmHg
Flash Point: 227.6 °C
Solubility:
Appearance: White or almost White Crystalline power
Hazard Symbols: ToxicT
Risk Codes: 61
Safety: 53-22-36/37/39-45
Transport Information:
PSA: 60.44000
LogP: 5.96960
Synthetic route
2051-49-2

n-hexanoic anhydride

68-96-2

17-hydroxyprogesterone

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With toluene-4-sulfonic acid
94201-44-2

17-hexanoyloxy-3β-hydroxy-pregn-5-en-20-one

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide
With cyclohexanone; aluminum isopropoxide
6084-02-2

3β-formyloxy-17-hexanoyloxy-pregn-5-en-20-one

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide
With cyclohexanone; aluminum isopropoxide
68-96-2

17-hydroxyprogesterone

142-62-1

hexanoic acid

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With trifluoroacetic anhydride
Stage #1: 17-hydroxyprogesterone; hexanoic acid With pyridine; toluene-4-sulfonic acid In toluene at 110 - 120℃; for 3h;
Stage #2: With hydrogenchloride In ethanol; water for 2h; Reagent/catalyst; Solvent; Reflux;
19.8 g
2051-49-2

n-hexanoic anhydride

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid; benzene
2: cyclohexanone; aluminium isopropylate
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid
2: hydrogenchloride
3: cyclohexanone; aluminum isopropoxide
View Scheme
20867-15-6

3β-formyloxy-17-hydroxy-pregn-5-en-20-one

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid; benzene
2: cyclohexanone; aluminium isopropylate
View Scheme
86790-83-2

3β-acetoxy-17-hexanoyloxy-pregn-5-en-20-one

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride
2: cyclohexanone; aluminum isopropoxide
View Scheme
68-96-2

17-hydroxyprogesterone

142-62-1

hexanoic acid

A

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

B

C33H50O5

Conditions
ConditionsYield
With pyridine; toluene-4-sulfonic acid In toluene at 110 - 120℃; for 3h; Solvent;
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

1096-38-4

16-dehydroprogesterone

Conditions
ConditionsYield
83%
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

4975-65-9

17α-Hydroxypregna-4,6-diene-3,20-dione 17-capronate

Conditions
ConditionsYield
With acetic anhydride; chloranil; 5-sulfosalicylic Acid In xylene for 6h; Heating;40%
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

5588-40-9

17-hexanoyloxy-pregna-1,4-diene-3,20-dione

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

A

anti-17α-Caproyloxy-Δ4-pregnen-20-on-3-N-chlorimin

B

syn-17α-Caproyloxy-Δ4-pregnen-20-on-3-N-chlorimin

Conditions
ConditionsYield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, OTs; Multistep reaction;
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Hexanoic acid (8R,9S,10R,13S,14S,17R)-3-acetoxy-17-acetyl-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

A

Hexanoic acid (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

B

Hexanoic acid (6R,8R,9S,10R,13S,14S,17R)-17-acetyl-6-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
at 37℃; for 0.166667h; in incubation mixture, with rat liver microsomes; or perbenzoic acid oxidation of dienol acetate;
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

81089-15-8

3β,17α-Dihydroxypregna-4,6-dien-20-one 17-caproate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 40 percent / chloranil, sulfosalicylic acid, acetic anhydride / xylene / 6 h / Heating
2: 55 percent / sodium borohydride / methanol / 0.5 h / Ambient temperature
View Scheme
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Hexanoic acid (6S,8R,9S,10R,13S,14S,17R)-6-acetoxy-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: acetic acid / Ambient temperature; anodic oxidation; platinum electrode, potassium acetate electrolyte
View Scheme
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

Hexanoic acid (6R,8R,9S,10R,13S,14S,17R)-6-acetoxy-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: acetic acid / Ambient temperature; anodic oxidation; platinum electrode, potassium acetate electrolyte
View Scheme
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1096-38-4
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Chemistry

Molecule structure of Hydroxyprogesterone caproate (CAS NO.630-56-8):

IUPAC Name: [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate 
Molecular Weight: 428.6041 g/mol
Molecular Formula: C27H40O4 
Density: 1.1 g/cm3 
Melting Point: 119 °C
Boiling Point: 536.4 °C at 760 mmHg 
Flash Point: 227.6 °C
Index of Refraction: 1.533
Molar Refractivity: 120.62 cm3
Molar Volume: 388.6 cm3
Surface Tension: 43.1 dyne/cm
Enthalpy of Vaporization: 81.31 kJ/mol
Vapour Pressure: 1.4E-11 mmHg at 25 °C
XLogP3: 5.7
H-Bond Acceptor: 4
Rotatable Bond Count: 7
Tautomer Count: 10
Exact Mass: 428.29266
MonoIsotopic Mass: 428.29266
Topological Polar Surface Area: 60.4
Heavy Atom Count: 31
Canonical SMILES: CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
Isomeric SMILES: CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]4C)C)C(=O)C
InChI: InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
InChIKey: DOMWKUIIPQCAJU-LJHIYBGHSA-N
EINECS: 211-138-8
Product Categories: Biochemistry; Hydroxyketosteroids; Steroids

Uses

 Hydroxyprogesterone caproate (CAS NO.630-56-8) is used as progesterone medicine.

Production

 Hydroxyprogesterone caproate can be prepared by the following sequence:

Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 399.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Safety Profile

Hazard Codes: ToxicT
Risk Statements: 61 
R61:May cause harm to the unborn child.
Safety Statements: 53-22-36/37/39-45 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: TU5085000
Human reproductive effects by an unknown route: behavioral effects on newborn. Experimental teratogenic and reproductive effects. Questionable carcinogen. A steroid. Used to treat menstrual disorders, threatened abortion, and sterility. When heated to decomposition it emits acrid smoke and fumes.

Specification

 Hydroxyprogesterone caproate (CAS NO.630-56-8) is also named as 17-((1-Oxohexyl)oxy)pregn-4-ene-3,20-dione ; 17-Hydroxypregn-4-ene-3,20-dione hexanoate ; 17-alpha-Hexanoyloxypregn-4-ene-3,20-dione ; 17-alpha-Hydroxy progesterone n-caproate ; 17-alpha-Hydroxyprogesterone caproate ; 17-alpha-Hydroxyprogesterone hexanoate ; 17alpha-Caproyloxypregn-4-ene-3,20-dione ; 17alpha-Hydroxyprogesterone caproate ; Caproate d'hydroxyprogesterone ; Caproate d'hydroxyprogesterone [INN-French] ; Caproato de hidroxiprogesterona ; Caproato de hidroxiprogesterona [INN-Spanish] ; Corlutin L.A. ; Delalutin ; Depo-Proluton ; Duraluton ; Estralutin ; Gesterol LA 250 ; Hylutin ; Hyproval ; Hyproval-PA ; Hyroxon ; Idrogestene ; Neolutin ; Neolutin forte ; Proge ; Progesterone caproate ; Progesterone retard pharlon ; Progesterone, 17-hydroxy-, hexanoate ; Proluton depot ; Relutin . Hydroxyprogesterone caproate (CAS NO.630-56-8) is an ester derivative of 17α-hydroxyprogesterone formed from caproic acid (hexanoic acid).