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Cas Database |
| Name |
7-Hydroxy cholesterol |
EINECS | N/A |
| CAS No. | 566-27-8 | Density | 1.03 g/cm3 |
| PSA | 40.46000 | LogP | 6.35950 |
| Solubility | N/A | Melting Point |
165-167?C |
| Formula | C27H46O2 | Boiling Point | 515.3 ºC at 760 mmHg |
| Molecular Weight | 402.661 | Flash Point | 214.7 ºC |
| Transport Information | N/A | Appearance | N/A |
| Safety | 22-26 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Cholest-5-ene-3b,7b-diol (8CI);7b-Hydroxycholest-5-en-3b-ol;7b-Hydroxycholesterol;D5-Cholestene-3b,7b-diol; |
Article Data | 41 |
7-Hydroxy cholesterol Synthetic route
- 17974-80-0
3β,7β-cholest-5-ene-3,7-diol-3-benzoate
- 566-27-8
cholest-5-en-3β,7β-diol
| Conditions | Yield |
|---|---|
| With sodium carbonate In methanol; water for 0.5h; Heating; | 100% |
| With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran for 48h; Heating; | 90 mg |
- 17974-77-5
3β-acetoxy-7β-hydroxycholest-5-ene
- 566-27-8
cholest-5-en-3β,7β-diol
| Conditions | Yield |
|---|---|
| With water; sodium hydroxide In ethanol; dichloromethane at 20℃; for 2h; | 95% |
| With sodium carbonate In methanol; water at 25℃; Inert atmosphere; |
- 18099-24-6
cholest-5-ene-3β,7β-diol diacetate
- 566-27-8
cholest-5-en-3β,7β-diol
| Conditions | Yield |
|---|---|
| With sodium hydroxide In methanol at 20℃; Deacetylation; | 87% |
- 809-51-8
7-ketocholesteryl acetate
A
- 566-26-7
(3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
B
- 566-27-8
cholest-5-en-3β,7β-diol
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran at 65℃; for 2h; | A 80% B n/a |
| With aluminum isopropoxide; isopropyl alcohol Behandeln der Reaktionsloesung mit wss. KOH bei Raumtemperatur; | |
| With lithium aluminium tetrahydride |
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 2h; | 79% |
| With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol for 0.166667h; Ambient temperature; | 78% |
| With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol at 20℃; for 1h; | 75% |
| With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 0 - 20℃; for 4h; Inert atmosphere; | 58% |
| Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0 °C 2: 1) 1M L-Selectride, 2) 6 M aq. NaOH, 30percent H2O2 / 1) THF, -78 deg C, 5 h, 2) THF, H2O, r.t., 1 h 3: 90 mg / nBu4NBr, 0.5 M aq. NaOH / tetrahydrofuran / 48 h / Heating View Scheme |
| Conditions | Yield |
|---|---|
| With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In dichloromethane at 23℃; for 48h; Catalytic behavior; Time; Temperature; chemoselective reaction; | A 53% B 15% |
- 75-91-2
tert.-butylhydroperoxide
- 57-88-5
cholesterol
A
- 566-28-9
7-Oxocholesterol
B
- 36871-91-7, 75671-16-8, 75671-17-9, 86900-29-0, 2846-29-9
3β-hydroxycholest-5-ene-7α-hydroperoxide
C
- 566-26-7
(3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
D
- 566-27-8
cholest-5-en-3β,7β-diol
E
- 36871-91-7
7β-hydroperoxy-3β-hydroxycholest-5-ene
| Conditions | Yield |
|---|---|
| Rh2(cap)4 In dichloromethane at 25℃; for 15h; Allylic oxidation; | A 30% B 10% C 12% D 3% E 4% |
- 57-88-5
cholesterol
A
- 566-28-9
7-Oxocholesterol
B
- 36871-91-7, 75671-16-8, 75671-17-9, 86900-29-0, 2846-29-9
3β-hydroxycholest-5-ene-7α-hydroperoxide
C
- 566-26-7
(3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
D
- 566-27-8
cholest-5-en-3β,7β-diol
E
- 36871-91-7
7β-hydroperoxy-3β-hydroxycholest-5-ene
| Conditions | Yield |
|---|---|
| With tert.-butylhydroperoxide; [Rh2(cap)4*2CH3CN] In water; 1,2-dichloro-ethane at 25℃; for 15h; | A 30% B 10% C 12% D 3% E 4% |
- 57-88-5
cholesterol
A
- 566-28-9
7-Oxocholesterol
B
- 566-27-8
cholest-5-en-3β,7β-diol
C
- 2953-38-0, 4025-59-6, 24116-45-8, 55700-78-2, 75764-48-6, 97100-48-6, 114246-94-5, 134356-45-9, 1250-95-9
5beta,6beta-Epoxycholestanol
D
- 1250-95-9
5α,6α-epoxycholestan-3β-ol
| Conditions | Yield |
|---|---|
| at 150℃; Further byproducts given; | A 21.9% B 13% C 7.4% D 10.8% |
| at 150℃; Further byproducts given; | A 21.9% B 13% C 7.4% D 10.8% |
| at 150℃; for 1h; |
7-Hydroxy cholesterol Specification
The IUPAC name of 7-Hydroxy cholesterol is (7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol. With the CAS registry number 566-27-8, it is also named as Cholest-5-ene-3,7-diol, (3beta,7beta)-. The product's categories are hydroxycholesterol, intermediates & fine chemicals, pharmaceuticals and steroids. In addition, its molecular formula is C27H46O2 and molecular weight is 402.65. Moreover, this chemical is used as a metabolite of Cholesterol.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 7.94; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.94; (4)ACD/LogD (pH 7.4): 7.94; (5)ACD/BCF (pH 5.5): 634835.13; (6)ACD/BCF (pH 7.4): 634835.13; (7)ACD/KOC (pH 5.5): 495581.5; (8)ACD/KOC (pH 7.4): 495581.5; (9)H bond acceptors: 2; (10)H bond donors: 2; (11)Freely Rotating Bonds: 7; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 121.48 cm3; (15)Molar Volume: 389.3 cm3; (16)Polarizability: 48.16×10-24cm3; (17)Surface Tension: 41.4 dyne/cm; (18)Density: 1.03 g/cm3; (19)Flash Point: 214.7 °C; (20)Enthalpy of Vaporization: 90.6 kJ/mol; (21)Boiling Point: 515.3 °C at 760 mmHg; (22)Vapour Pressure: 8.93E-13 mmHg at 25 °C.
When you are using this chemical, please be cautious about it as the following: 7-Hydroxy cholesterol is harmful if swallowed and very toxic by inhalation.
People can use the following data to convert to the molecule structure.
SMILES:CC(C)CCC[C@@H](C)[C@H]3CC[C@H]2[C@@H]4[C@@H](O)/C=C1/C[C@@H](O)CC[C@]1(C)[C@H]4CC[C@@]23C
InChI:InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
InChIKey:OYXZMSRRJOYLLO-KGZHIOMZBE
Std. InChI:InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
Std. InChIKey:OYXZMSRRJOYLLO-KGZHIOMZSA-N
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