Cholestanone
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MedKoo CAT#: 574275

CAS#: 601-57-0

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. 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 due to induction of hypertrophy and reduction in the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.

Chemical Structure

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Cholestanone
CAS# 601-57-0
Instruction

Theoretical Analysis

MedKoo Cat#: 574275
Name: Cholestanone
CAS#: 601-57-0
Chemical Formula: C27H44O
Exact Mass: 384.34
Molecular Weight: 384.650
Elemental Analysis: C, 84.31; H, 11.53; O, 4.16

Price and Availability

Size Price Availability Quantity
5g USD 300 2 Weeks
10g USD 550 2 Weeks
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Synonym: Δ4-Cholestenone, Cholestanone, NSC 63000, NSC 134926

IUPAC/Chemical Name: cholest-4-en-3-one

InChi Key: NYOXRYYXRWJDKP-GYKMGIIDSA-N

InChi Code: 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

SMILES Code: O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C)=C1

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 384.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1. Salen, G., Batta, A.K., Tint, G.S., et al. Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemia. J. Lipid Res. 35(10), 1878-1887 (1994).

2. Chen, C.-L., Wu, D.-C., Liu, M.-Y., et al. Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cells. J. Recept. Signal Transduct. Res. 37(2), 189-199 (2017).

3. Steinberg, D., Fredrickson, D.S., and Avigan, J. Effects of Δ4-cholestenone in animals and in man. Proc. Soc. Exp. Biol. Med. 97(4), 784-790 (1958).

4. Wu, K., Li, W., Song, J., et al. Production, purification, and identification of cholest-4-en-3-one produced by cholesterol oxidase from Rhodococcus sp. in aqueous/organic biphasic system. Biochem. Insights 8(Suppl 1), 1-8 (2015).