| Identification | More | [Name]
4-Cholesten-3-one | [CAS]
601-57-0 | [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
3-KETO-4-CHOLESTENE
(+)-3-OXO-4-CHOLESTENE
3-OXO-4-CHOLESTENE
(+)-4-CHOLESTEN-3-ONE
4-CHOLESTEN-3-ONE
(8S,9S,10R,13R,14S,17R)-17-((R)-1,5-DIMETHYL-HEXYL)-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE
CHOLEST-4-ENE-3-ONE
CHOLESTENONE
3-Oxocholest-4-ene
4-Cholestenone
cholest-4-en-3-one
delta4-Cholesten-3-one
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
10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
4-CHOLESTEN-3-ONE, 98+%
(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
3-Keto-4-cholestene, 3-Oxo-4-cholestene
3-Keto-4-cholestene, 3-Oxo-4-cholestene, 4-Cholesten-3-one | [EINECS(EC#)]
210-005-1 | [Molecular Formula]
C27H44O | [MDL Number]
MFCD00003663 | [Molecular Weight]
384.64 | [MOL File]
601-57-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystals or powder | [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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Optical Rotation]
[α]23/D +91.0°, c = 2 in chloroform | [Water Solubility ]
<0.5 g/L | [BRN ]
4707774 | [InChI]
1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1 | [InChIKey]
NYOXRYYXRWJDKP-GYKMGIIDSA-N | [SMILES]
[H][C@@]12[C@]([C@](CC3)(C)C(CC2)=CC3=O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)C | [CAS DataBase Reference]
601-57-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Cholest-4-en-3-one(601-57-0) | [EPA Substance Registry System]
601-57-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard statements ]
H413 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
FZ7700000
| [TSCA ]
Yes | [HS Code ]
29142900 | [Storage Class]
11 - Combustible Solids |
| Material Safety Data Sheet(MSDS) | Back Directory | [msds information]
(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(601-57-0).msds |
| Hazard Information | Back Directory | [Description]
Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol.1 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.2 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.3 It has been used as synthetic intermediate in the synthesis of steroids.4 | [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. | [storage]
Store at -20°C | [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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