5α-Cholestane
- Product Name
- 5α-Cholestane
- CAS No.
- 481-21-0
- Chemical Name
- 5α-Cholestane
- Synonyms
- CHOLESTANE;NSC 224419;α-Cholestane;5α-Cholestane;5-α-cholestane;Cholestane(5α);(5A)-CHOLESTANE;alpha-Cholestane;5ALPHA-CHOLESTANE;Cholestane, (5α)-
- CBNumber
- CB3239829
- Molecular Formula
- C27H48
- Formula Weight
- 372.67
- MOL File
- 481-21-0.mol
5α-Cholestane Property
- Melting point:
- 78-80 °C
- Boiling point:
- 250 °C (1 mmHg)
- Density
- 0.9090
- refractive index
- 1.4887
- storage temp.
- room temp
- solubility
- DMF: 1 mg/ml
DMSO: 0.1 mg/ml
Ethanol: 20 mg/ml
Ethanol: PBS (pH 7.2)(1:2): 0.1 mg/mlPBS (pH 7.2): 0.1 mg/ml - form
- Crystalline Powder
- color
- White
- Merck
- 13,2219
- BRN
- 2051806
- InChI
- 1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21-,22+,23-,24+,25+,26+,27-/m1/s1
- InChIKey
- XIIAYQZJNBULGD-XWLABEFZSA-N
- SMILES
- CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C
- LogP
- 11.945 (est)
- CAS DataBase Reference
- 481-21-0(CAS DataBase Reference)
- EPA Substance Registry System
- Cholestane, (5.alpha.)- (481-21-0)
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-38-40-48/20/22-67-36/38-20-63
- Safety Statements
- 24/25-36/37-26
- RIDADR
- UN 1888 6.1/PG 3
- WGK Germany
- 3
- HS Code
- 29021990
- Storage Class
- 11 - Combustible Solids
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H331Toxic if inhaled
H336May cause drowsiness or dizziness
H351Suspected of causing cancer
H372Causes damage to organs through prolonged or repeated exposure
H412Harmful to aquatic life with long lasting effects
- Precautionary statements
-
P201Obtain special instructions before use.
P273Avoid release to the environment.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P308+P313IF exposed or concerned: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- C8003
- Product name
- 5α-Cholestane
- Purity
- ≥97.0% (HPLC)
- Packaging
- 1g
- Price
- $195.04
- Updated
- 2025/07/31
- Product number
- C8003
- Product name
- 5α-Cholestane
- Purity
- ≥97.0% (HPLC)
- Packaging
- 5g
- Price
- $836
- Updated
- 2025/07/31
- Product number
- 47124
- Product name
- 5-α-Cholestane
- Purity
- certified reference material, 10?mg/mL in chloroform
- Packaging
- 1ML
- Price
- $53.29
- Updated
- 2025/07/31
- Product number
- R205370
- Product name
- 5-ALPHA-CHOLESTANE
- Purity
- AldrichCPR
- Packaging
- 1MG
- Price
- $139
- Updated
- 2024/03/01
- Product number
- 26763
- Product name
- 5α-Cholestane
- Packaging
- 500mg
- Price
- $92
- Updated
- 2024/03/01
5α-Cholestane Chemical Properties,Usage,Production
Description
5α-Cholestane is a sterol that has been found in dust samples from urban and rural paved and agricultural and public unpaved roads. It has been used as an internal standard for the quantification of phytosterols by HPLC-MS/MS and fecal sterols by GC-FID and GC-MS.
Chemical Properties
WHITE CRYSTALLINE POWDER
Uses
5α-Cholestane was used as standard in cholesterol analysis by GC and HPLC.
Uses
α-Cholestane is the trans-decalin homolog of Coprostane.
Definition
ChEBI: The 5alpha-stereoisomer of cholestane.
Biochem/physiol Actions
5α-Cholestane is a sterol produced endogenously from cholesterol and has been isolated from human feces. It is derived from cholesterol by the action of intestinal microorganisms. Derivatives of 5α-cholestane in plants are called Brassinosteroids that selectively activate the PPI3K/Akt pathway.
Synthesis
In a reaction flask equipped with a stirrer, thermometer, ventilating duct, and reflux condenser (with calcium chloride drying tube), add 250 mL of anhydrous ether, cool to -10 to -15C, and slowly pass the hydrogen chloride into the body for about 45 min. and then add cholesterol ketone at -15C
(2) 10 g (0.0216 mol). The reaction mixture was then cooled to -20C and 12.3 g (0.19 mol) of active zinc (1) was added in 2 to 3 minn. The temperature was slowly increased to -5C and the reaction was stirred at -5 to 0C for 2 h. The reaction was then cooled to -15C and the reaction was slowly poured into 130 g of crushed ice with thorough stirring. The organic layer was separated and the aqueous layer was extracted with ether. The ether solutions were combined, washed with saturated sodium chloride and dried over anhydrous sodium sulfate. The ether was evaporated to give a colorless liquid, which solidified on cooling. The solid was dissolved in 30-40mL of hexane, passed over a silica gel column and eluted with hexane. Hexane was evaporated under reduced pressure to give 8 to 8.2 g of cholestane
(1) in 82% to 84% yield. Recrystallized with ethanol-ether, obtained flaky crystals 7.3-7.5g, mp 78-79C. Note: Activated zinc can be prepared as follows: 16g of zinc powder which passes through 300 mesh sieve is soaked in 100mL of 2% hydrochloric acid for about 4min until the surface of the zinc powder is shiny. Pour off the dilute hydrochloric acid and wash with distilled water 4 times. Filtered, washed with sufficient water, and then washed with ethanol, acetone and ether sequentially. And then dried in vacuum at 85 ~ 90 to obtain 13 ~ 14 g of active zinc, immediately used in the reaction.
Purification Methods
Crystallise 5-cholestane from Et2O/EtOH or EtOAc. [Ruzicka et al. Helv Chim Acta 16 327 1933, Beilstein 5 III 1132, 5 IV 1227.]
References
[1] W. ROGGE B S P Medeiros. Organic Compounds in Dust from Rural and Urban Paved and Unpaved Roads Taken During the San Joaquin Valley Fugitive Dust Characterization Study[J]. Environmental Engineering Science, 2012, 25 1: 1-13. DOI: 10.1089/ees.2010.0124
[2] SUKANYA MINGYAI. Effects of Extraction Methods on Phytochemicals of Rice Bran Oils Produced from Colored Rice.[J]. Journal of oleo science, 2018, 67 2: 135-142. DOI: 10.5650/jos.ess17122
[3] CAROLINE SCHNNING; Thor A S; Rhys Leeming. Faecal contamination of source-separated human urine based on the content of faecal sterols[J]. Water Research, 2002, 36 8: Pages 1965-1972. DOI: 10.1016/s0043-1354(01)00427-4
5α-Cholestane Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5α-Cholestane manufacturers
- Product
- 5α-Cholestane 481-21-0
- Price
- US $1.00/KG
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2018-12-24