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4-Cholesten-3-one

4-Cholesten-3-one structure

CAS No:
601-57-0
Formula:
C27H44O
Chemical Name:
4-Cholesten-3-one
Synonyms:
17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecah;17-(1,5-DIMETHYLHEXYL)-10,13-DIMETHYL-2,3,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-ONE;4-CHOLESTEN-3-ONE;3-KETO-4-CHOLESTENE;3-OXO-4-CHOLESTENE;CHOLEST-4-ENE-3-ONE;CHOLESTENONE;3-Oxocholest-4-ene
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Cholestenone is the intermediate oxidation product of cholesterol.

Δ4-Cholesten-3-one is an intestinal metabolite of Cholesterol with anti-obesity effect on animals.

Solid

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.

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.

4-Cholesten-3-one Basic Attributes

Molecular Weight：

384.64

Exact Mass：

384.64

BRN：

4707774

EC Number：

210-005-1

UNII：

7T94NHD99C

TSCA：

TSCA listed

DSSTox ID：

DTXSID90872379

Color/Form：

White to Off-White

HScode：

29142900

Characteristics

PSA：

17.07000

XLogP3：

9.36

Appearance：

Solid

Density：

0.9717 (rough estimate)

Melting Point：

79-82 °C

Boiling Point：

451.27°C (rough estimate)

Flash Point：

247.7±10.4 °C

Refractive Index：

1.5100 (estimate)

Water Solubility：

<0.5 g/L

Storage Conditions：

Store in a cool, dry place. Store in a tightly closed container.

Critical Temperature & Pressure：

-20°C

Safety Information

wgk germany：

hazard class code：

safety instructions：

22-24/25-36-26

RTECS Number：

FZ7700000

Marks：

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P273, P501

Hazard Statements：

36/37/38

GHS Classification：

H413 (97.44%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Name	Type of Test	Exposure Route	Species Observed	Dose/Duration	Toxic Effects	Reference
MUTATION DATA	Sister chromatid exchange	Rectal		94 mg/kg	--	Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 8(Suppl 6),41,1986

Drug Information

MeSH Entry Terms：

4-cholesten-3-one

4-Cholesten-3-one Use and Manufacturing

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.

Manufacturing Info：

Cholest-4-en-3-one: ACTIVE

Use Classification：

Human drugs -> Rare disease (orphan)|Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]

Computed Properties

Molecular Weight:384.6
XLogP3:8.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:384.339216023
Monoisotopic Mass:384.339216023
Topological Polar Surface Area:17.1
Heavy Atom Count:28
Complexity:630
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

1232680-81-7

2469-23-0

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Guide of 4-Cholesten-3-one

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Synthesis Route
Recommended Suppliers
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4-Cholesten-3-one

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