Basic information
- CAS
360-68-9- Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
QYIXCDOBOSTCEI-NWKZBHTNSA-N- Molecular formula
- C27H48O
- Average molar mass
- 388.7 g/mol
- Monoisotopic mass
- 388.37051615
Overview
Coprostanol is a member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position. It has a role as a plant metabolite, an environmental contaminant and a human urinary metabolite. It is a member of phytosterols, a 3-hydroxy steroid and a cholestanoid. It derives from a hydride of a 5beta-cholestane.
Names & identifiers
- Preferred name
- Coprostanol
- IUPAC
- (3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- COPROSTANOL
- Molecular formula
- C27H48O
- Molecular weight
- 388.68
Names & synonyms
CoprosterolCOPROSTANOL360-68-9Stercorin5beta-Cholestan-3beta-olKoprosterinKoprosterolPPT67I3S74NSC-5060NSC-18175DTXSID1052036CHEBI:89519
Show more names
ZymostanolCholestan-3-olCOPROSTAN-3B-OL5beta-cholestanol
(3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-olCholestan-3-ol, (3beta,5beta)-(3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-olRefChem:127930DTXCID6030603206-638-8Coprostan-3-ol5-beta-Cholestan-3-beta-ol
Database identifiers
- CAS
360-68-9- PubChem CID
- 221122
- DTXSID
DTXSID1052036- ChEMBL
CHEMBL2048325- ChEBI
CHEBI:89519- UNII
- PPT67I3S74
- EC Number
- 206-638-8
Properties
Computed structural properties
- XLogP
- 9.4
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 540
Experimental & physicochemical properties
Chemical Classes
Biological Agents -> Cholesterol and Derivatives
Hormone and(or) waste-water effluent contaminant
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Melting Point102 °C
Physical Description
Solid; [Merck Index]
Solid
Physicochemical properties
- Melting point
- 101 ° · 101°
- alpha
- 18 · D18 +28° (c = 1.8 in CHCl3)
- Boiling point
- 454.32 °C · 454.32°C (rough estimate)
- Density
- 0.9506 · 0.9506 (rough estimate)
- refractive index
- 1.525 · 1.5250 (estimate)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Ethylacetate (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.
Not Classified
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Toxicology
USGS Health-Based Screening Levels for Evaluating Water-Quality
3-beta-Coprostanol
Hormone and(or) waste-water effluent contaminant
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsIntestine
Cellular LocationsExtracellular
Uses & manufacturing
UsesDetected in feces of humans and carnivores; [Merck Index] Main sterol of the feces produced by the reduction of cholesterol by intestinal bacteria. [Stedman's Medical Dictionary]
Applications
UsesCoprostan-3-ol is a 27-carbon stanol resulted from biohydrogenation of cholesterol in the gut of most higher animals. It is a common biomarker for the presence of human faecal matter in the environment (1,2).This compound is a contaminant of emerging concern (CECs).
UsesIt has been used as an internal standard for the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC/MS.
General DescriptionCoprostan-3-ol is a cholesterol derivative that can be prepared from 5β-cholestan-3-one via reduction.
Suppliers31 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [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]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Aladdin Scientific
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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