4-Cholesten-3-one Chemical Properties

Melting point:

79-82 °C

alpha 

92.5 º (c=2, CHCl3)

Boiling point:

451.27°C (rough estimate)

Density 

0.9717 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

-20°C

solubility 

Chloroform (Sparingly), Methanol (Slightly, Heated)

form 

Solid

color 

White to Off-White

optical activity

[α]23/D +91.0°, c = 2 in chloroform

Water Solubility 

<0.5 g/L

BRN 

4707774

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

601-57-0(CAS DataBase Reference)

NIST Chemistry Reference

Cholest-4-en-3-one(601-57-0)

EPA Substance Registry System

Cholest-4-en-3-one (601-57-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

FZ7700000

TSCA 

Yes

HS Code 

29142900

MSDS

• Language:English Provider:(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Cholesten-3-one Usage And Synthesis

Description

Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.

Chemical Properties

white to light yellow crystals or powder

Uses

4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.

Definition

ChEBI: Cholest-4-en-3-one is a cholestanoid that is cholest-4-ene substituted by an oxo group at position 3. It has a role as a human metabolite and a plant metabolite. It is a cholestanoid and a 3-oxo-Delta(4) steroid.

General Description

Cholestenone is a cholesterol metabolite and analog, which substitutes membrane cholesterol and elevates membrane fluidity.

References

[1] G SALEN. Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemia.[J]. Journal of Lipid Research, 1994, 35 10: 1878-1887.
[2] CHUN-LIN CHEN. Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cells.[J]. Journal of Receptors and Signal Transduction, 2017, 37 2: 189-199. DOI: 10.1080/10799893.2016.1203944
[3] D STEINBERG  J A  D S FREDRICKSON. Effects of 4-cholestenone in animals and in man.[J]. Proceedings of the Society for Experimental Biology and Medicine, 1958, 97 4: 784-790. DOI: 10.3181/00379727-97-23880
[4] KE WU. Production, Purification, and Identification of Cholest-4-en-3-one Produced by Cholesterol Oxidase from Rhodococcus sp. in Aqueous/Organic Biphasic System.[J]. Biochemistry Insights, 2015, 8 Suppl 1: 1-8. DOI: 10.4137/bci.s21580

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• 2BETA,3BETA,14ALPHA,22[R],25-PENTAHYDROXY-7-CHOLESTEN-6-ONE,2β,3β,14α,22(r),25-pentahydroxy-7-cholesten-6-one