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11-alpha-Hydroxycarvenone
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Name

11-alpha-Hydroxycarvenone

 EINECS 606-276-4
CAS No. 192569-17-8 Density 1.25 g/cm3
PSA 63.60000 LogP 3.34090
Solubility N/A Melting Point 232-234°C
Formula C22H28O4 Boiling Point 584.7 °C at 760 mmHg
Molecular Weight 356.462 Flash Point 207.3 °C
Transport Information N/A Appearance yellow crystalline solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 192569-17-8 (11-alpha-Hydroxycarvenone) Hazard Symbols N/A
Synonyms

(11a,17a)-11,17-Dihydroxy-3-oxo-pregna-4,6-diene-21-carboxylic acid;

Article Data 3

11-alpha-Hydroxycarvenone Synthetic route

976-71-6

canrenone

192569-17-8

11α-hydroxyl canrenone

Conditions
ConditionsYield
With D-glucose; peptone In water90%
With D-glucose In water for 72h;80%
With D-glucose In water for 72h;80%
Reaxys ID: 13210058

Reaxys ID: 13210058

192569-17-8

11α-hydroxyl canrenone

976-71-6

canrenone

A

192569-17-8

11α-hydroxyl canrenone

B

1363502-03-7

C22H28O5

Conditions
ConditionsYield
With Aspergillus ochraceus SIT34205 at 28℃; for 50h;
192569-17-8

11α-hydroxyl canrenone

124-63-0

methanesulfonyl chloride

209253-91-8

11α-(methylsulphonyl)oxy-canrenone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h;98%
192569-17-8

11α-hydroxyl canrenone

75-52-5

nitromethane

1398078-03-9

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
With benzalkonium chloride; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 48h; stereoselective reaction;90%
With benzalkonium chloride; potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 48h; Reagent/catalyst;90%
534-22-5

2-methylfuran

192569-17-8

11α-hydroxyl canrenone

610785-47-2

11α,17β-dihydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone

Conditions
ConditionsYield
With ethanol; boron trifluoride diethyl etherate In nitromethane; dichloromethane at -17℃; for 20h;86.2%
With ethanol; boron trifluoride diethyl etherate In nitromethane at -20 - -17℃; for 20h;
192569-17-8

11α-hydroxyl canrenone

75-52-5

nitromethane

A

1398078-03-9

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

B

1398078-09-5

11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; Reagent/catalyst; Temperature; Time;A 25%
B 15%
192569-17-8

11α-hydroxyl canrenone

143-33-9

sodium cyanide

192704-54-4

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile

Conditions
ConditionsYield
With sulfuric acid In ISOPROPYLAMIDE; water at 95℃; for 18.5h;3 g
192569-17-8

11α-hydroxyl canrenone

610785-45-0

5α,17β-dihydroxy-3-oxo-pregn-9(11)-ene-7α,21-dicarboxylic acid bis-γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
4: potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol; water / 14 h / 20 - 50 °C
5: methyltrifluoromethyldioxirane / dichloromethane / 2 h / -25 °C
6: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve
View Scheme
192569-17-8

11α-hydroxyl canrenone

C28H42O4Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
View Scheme

11-alpha-Hydroxycarvenone Specification

The 11-alpha-Hydroxycarvenone, with the CAS registry number 192569-17-8, is also known as (11α,17α)-11,17-Dihydroxy-3-oxo-pregna-4,6-diene-21-carboxylic acid. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. This chemical's molecular formula is C22H28O4 and molecular weight is 356.46. Its IUPAC name is called (10R,11R,13S,17R)-11-hydroxy-10,13-dimethyl-spiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-tetrahydrofuran]-2',3-dione.

Physical properties of 11-alpha-Hydroxycarvenone: (1)ACD/LogP: 1.21; (2)ACD/LogD (pH 5.5): 1.21; (3)ACD/LogD (pH 7.4): 1.21; (4)ACD/BCF (pH 5.5): 4.86; (5)ACD/BCF (pH 7.4): 4.86; (6)ACD/KOC (pH 5.5): 107.91; (7)ACD/KOC (pH 7.4): 107.91; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.598; (12)Molar Refractivity: 96.74 cm3; (13)Molar Volume: 283.4 cm3; (14)Surface Tension: 52.6 dyne/cm; (15)Density: 1.25 g/cm3; (16)Flash Point: 207.3 °C; (17)Enthalpy of Vaporization: 100.3 kJ/mol; (18)Boiling Point: 584.7 °C at 760 mmHg; (19)Vapour Pressure: 4.14E-16 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@]12CCC(=O)C=C1C=CC3C2[C@@H](C[C@]4(C3CC[C@@]45CCC(=O)O5)C)O
(2)InChI: InChI=1/C22H28O4/c1-20-8-5-14(23)11-13(20)3-4-15-16-6-9-22(10-7-18(25)26-22)21(16,2)12-17(24)19(15)20/h3-4,11,15-17,19,24H,5-10,12H2,1-2H3/t15?,16?,17-,19?,20+,21+,22-/m1/s1
(3)InChIKey: RJTDWMKVQUPGSY-GOAYFHFKBJ

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