Dihydrocholesterol Property

Melting point:

138-142 °C

alpha 

D22 +24.2° (c = 1.3 in chloroform)

Boiling point:

454.32°C (rough estimate)

Density 

0.9506 (rough estimate)

refractive index 

1.5250 (estimate)

storage temp. 

-20°C

solubility 

chloroform: 0.1 g/mL, clear, colorless

pka

15.14±0.70(Predicted)

form 

A solid

color 

White to off-white

Water Solubility 

Insoluble in water.

Merck 

14,2200

BRN 

2418594

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

LogP

10.065 (est)

CAS DataBase Reference

80-97-7(CAS DataBase Reference)

NIST Chemistry Reference

Cholestanol(80-97-7)

EPA Substance Registry System

Dihydrocholesterol (80-97-7)

Safety

Hazard Codes 

Xn

Risk Statements 

22-38-40-48/20/22-67-36/38-20-63

Safety Statements 

24/25-36/37-22-26

RIDADR 

UN 1888 6.1/PG 3

WGK Germany 

3

RTECS 

FZ6350000

TSCA 

Yes

HS Code 

2906 13 10

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

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P281Use personal protective equipment as required.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P311Call a POISON CENTER or doctor/physician.

Dihydrocholesterol Chemical Properties,Usage,Production

Description

Cholestanol is a cholesterol metabolite formed by oxidation and an intermediate in the biosynthesis of chenodeoxycholic acid . Cholestanol (10 μg/ml) induces apoptosis in cornea and lens epithelial cells and increases the activity of IL-1β converting enzyme (ICE) and CPP32 proteases. Dietary administration of 1% cholestanol to mice increases serum and liver cholestanol levels and leads to corneal opacities and gallstones and in rats it leads to cholestanol deposition in the cerebellum. Cholestanol levels are increased in plasma of patients with cerebrotendinous xanthomatosis (CTX), a disease characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.

Chemical Properties

white powder

Uses

5alpha-Cholestan-3beta-ol is used as a standard in lipid analysis using HPLC. It acts as a derivitized steroid compound. It is used in agrochemical, pharmaceutical and dyestuff field .

Uses

5α-Cholestan-3β-ol is a carbon stanol formed from biohydrogenation of Cholesterol (C432501) in the gut. Studies have also examined the conversion of 5α-Cholestan-3β-ol catalyzed by 3-β-hydroxysteroid dehydrogenase of rat liver.

Definition

ChEBI: A cholestanoid that is (5alpha)-cholestane substituted by a beta-hydroxy group at position 3.

General Description

Cholestanol is a 5α-dihydro derivative of cholesterol. It acts as a marker for cholesterol absorption. Cholestanol is a steroid with 27 carbon atoms.

Biochem/physiol Actions

5α-Cholestan-3β-ol is derived from cholesterol by the action of intestinal microorganisms. It is known to induce the formation of gall stones in rabbits in the presence of sodium ions.

Purification Methods

Purify 5--cholestan-3-ol via acetylation, crystallisation and de-acetylation, then recrystallisation from EtOH or slightly aqueous EtOH, or MeOH. Its solubility is: 0.5% (MeOH) and 1% (EtOH) at 25o. [Mizutani & Whitten J Am Chem Soc 107 3621 1985.] The acetate has m 114-115o from EtOAc/MeOH and, [] D 20 +13o (c 2, CHCl3). [Bruce & Ralls Org Synth Col Vol II 191 1943, Beilstein 6 IV 3577.]