Lathosterol

HCID 65728CAS 80-99-9
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Basic information

Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
IZVFFXVYBHFIHY-SKCNUYALSA-N
Molecular formula
C27H46O
Average molar mass
386.7 g/mol
Monoisotopic mass
386.35486609

Overview

5alpha-cholest-7-en-3beta-ol is a cholestanoid that is (5alpha)-cholest-7-ene substituted by a beta-hydroxy group at position 3. It has a role as a mouse metabolite and a human metabolite. It is a C27-steroid, a Delta(7)-sterol, a 3beta-sterol and a cholestanoid.

Names & identifiers

Preferred name
Lathosterol
IUPAC
(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
English name
LATHOSTEROL
Molecular formula
C27H46O
Molecular weight
386.65

Names & synonyms

Lathosterol80-99-95alpha-Cholest-7-en-3beta-olgamma-CholesterolCHEBI:17168DTXSID501015889(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-olRefChem:1524315 alpha-cholest-7-en-3 beta-olDTXCID901474047Cholest-7-en-3beta-ol
Show more names
-Cholestenolγ-CholestenolGAMMA-CHOLESTENOLCholest-7-en-3-olDELTA7-Cholestenol7-En-3-cholestanol5Α-CHOLEST-7-EN-3-OL
Cholest-7-en-3-ol, (3b,5a)-7-Cholesten-3-beta-olCholesterol EP Impurity A5|A-Cholest-7-en-3|A-ol5-alpha-Cholest-7-en-3-beta-ol(3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol7-CholesterolCholesterin [German]

Database identifiers

CAS
80-99-9
PubChem CID
65728
DTXSID
DTXSID501015889
ChEMBL
CHEMBL3138639
ChEBI
CHEBI:17168
Nikkaji
J9.827B

Properties

Computed structural properties

XLogP
8.3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
5
Heavy atoms
28

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Melting Point122.0 °C
Physical DescriptionSolid
Collision Cross Section · 2 items

204 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

204.5 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point
126 °C · 126°C
Boiling point
452.8 °C · 452.8°C (rough estimate)
Density
0.961 · 0.9610 (rough estimate)
refractive index
1.525 · 1.5250 (estimate)
storage temp.
-20 °C · -20°C
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)

Safety & regulation

Safety data

wgk
3
rtecs
FZ7000000
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

Tissue LocationsAdipose Tissue
Cellular LocationsEndoplasmic reticulum
Metabolite PathwaysAlendronate Action Pathway
Applications · 4 items

UsesA Cholesterol (C432501) metabolite. Lathosterol (indicating cholesterol synthesis) and Sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low Lathosterol, Sitosterol (S497050), and Cholesterol (C432501) predicted mortality additively and independently of each other.

UsesLathosterol has been used as a standard for the estimation of the concentrations of cholesterol and plant sterols.

Uses5α-Cholest-7-en-3β-ol was used as a substrate in enzymatic assay for plasma cholesterol. It was used to supplement diet of Daphnia galeata to study the effect on life-history traits.

General DescriptionLathosterol is a cholesterol synthesis precursor.

Upstream & downstream products

Suppliers50 total

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]

Additional notes

DefinitionChEBI: A cholestanoid that is (5alpha)-cholest-7-ene substituted by a beta-hydroxy group at position 3.

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