(24R)-5-Ergosten-3beta-ol
Basic information
- CAS
474-62-4- Standard SMILES
CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C- InChIKey
SGNBVLSWZMBQTH-UHFFFAOYSA-N- Molecular formula
- C28H48O
- Average molar mass
- 400.7 g/mol
- Monoisotopic mass
- 400.37051615
Overview
campesterol has been reported in Sideritis candicans, Strychnos cathayensis, and other organisms with data available.
Names & identifiers
- Preferred name
- (24R)-5-Ergosten-3beta-ol
- IUPAC
- 17-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- Campesterol
- Molecular formula
- C28H48O
- Molecular weight
- 400.69
Names & synonyms
(24R)-5-Ergosten-3beta-ol(24R)-5-Ergosten-3.beta.-olErgost-5-en-3.beta.-ol, (24R)-24.alpha.-MethylcholesterolCampesterol [M+H]+Ergost-5-en-3-ol #(24R)-5-Ergosten-3-olSCHEMBL168489Ergost-5-en-3-ol,24R)-NSC224330(24R)-Methylcholest-5-en-3beta-ol24alpha-Methyl-5-cholesten-3beta-ol
Show more names
CampesterinErgost-5-en-3-ol24α-methyl Cholesterol(24R)-Ergost-5-en-3β-olC01789CAMPESTROLCampasterolCampesterolMieyajunsu A-17-((2R,5R)
DB-05145117-(5,6-dimethylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Database identifiers
- CAS
474-62-4- PubChem CID
Properties
Computed structural properties
- XLogP
- 8.8
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 620
Physicochemical properties
- Melting point
- 156 · 156-160 °C
- alpha
- 23 · D23 -33° (22.5 mg in 5 ml chloroform)
- Boiling point
- 463.29 °C · 463.29°C (rough estimate)
- Density
- 0.98 · 0.98±0.1 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.51 · 1.5100 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Sparingly), Methanol (Slightly, Sonicated)
- form
- crystalline
- pka
- 15.03 · 15.03±0.70(Predicted)
- color
- white
- biological source
- Glycine max (soybean)
- Merck
- 13 · 13,1736
- BRN
- 3216975 · 3216975
- InChIKey
- SGNBVLSWZMBQTH-ZRUUVFCLSA-N
- SMILES
- [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)CC[C@H](C)C(C)C
- LogP
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN 1888 6.1/PG 3
- hs_code
- 29061990
- risk_code
- 20/21/22-36/37/38-48/20/22-40-38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T
- safety_code
- 26-36-45-36/37/39-23
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
Chemistry & industry
Applications
Description24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.
UsesA phytosterol, which may inhibit the intestinal absorption of cholesterol.
UsesCampesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.
General DescriptionCampesterol is a plant sterol, which is an analog of cholesterol and a brassinosteroid (BR) precursor. The enzyme diminute/dwarf1 mediates the synthesis of campesterol from 24-methylenecholesterol. Campesterol possesses methyl group at C-24 position of the side chain in the cholesterol structure.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane.
Related reactions
0 records
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Compound notes
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