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Merck

C7578

Coprostan-3-ol

≥98%

Synonym(s):

5β-Cholestan-3β-ol

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About This Item

Empirical Formula (Hill Notation):
C27H48O
CAS Number:
Molecular Weight:
388.67
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352001
EC Number:
206-638-8
MDL number:
Assay:
≥98%
Form:
powder
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Quality Level

assay

≥98%

form

powder

SMILES string

[H]C12CCC3C4CCC([C@@H](C)CCCC(C)C)C4(C)CCC3C1(C)CCC(O)C2

InChI

1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

QYIXCDOBOSTCEI-NWKZBHTNSA-N

General description

Coprostan-3-ol is a cholesterol derivative that can be prepared from 5β-cholestan-3-one via reduction.

Application

Coprostan-3-ol can be used as an internal standard:
  • For the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC-MS.
  • For GC-MS estimation of EpHβA (16-hydroxy-β-amyrin) content of leaves expressing SAD1 and CYP51H10 genes with a green fluorescent protein.

It has been used as an internal standard for the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC/MS.


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Characterization of placental cholesterol transport: ABCA1 is a potential target for in utero therapy of Smith-Lemli-Opitz syndrome.
Lindegaard ML, et al.
Human Molecular Genetics, 17(23), 3806-3813 (2008)
Matthew P Dale et al.
PloS one, 15(5), e0231980-e0231980 (2020-05-02)
Triterpenoids are high-value plant metabolites with numerous applications in medicine, agriculture, food, and home and personal care products. However, plants produce triterpenoids in low abundance, and their complex structures make their chemical synthesis prohibitively expensive and often impossible. As such
The reduction of 5a-cholestan-3-one and 5?-cholestan-3-one by some boranes and hydroborates.
Contreras R and Mendoza L.
Steroids, 34(2), 121-124 (1979)