MedKoo Cat#: 574275 | Name: Cholestanone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Cholestanone
Cholestanone
CAS#601-57-0

Theoretical Analysis

MedKoo Cat#: 574275

Name: Cholestanone

CAS#: 601-57-0

Chemical Formula: C27H44O

Exact Mass: 384.3392

Molecular Weight: 384.65

Elemental Analysis: C, 84.31; H, 11.53; O, 4.16

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
10g USD 600.00 2 Weeks
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Related CAS #
No Data
Synonym
Δ4-Cholestenone; Cholestanone; NSC 63000; NSC-63000; NSC63000; NSC 134926; NSC-134926; NSC134926;
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

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
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).