Basic information
- CAS
474-62-4- Standard SMILES
CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
SGNBVLSWZMBQTH-PODYLUTMSA-N- Molecular formula
- C28H48O
- Average molar mass
- 400.7 g/mol
- Monoisotopic mass
- 400.37051615
Overview
Campesterol is a 3beta-hydroxy-Delta(5)-steroid, a C28-steroid, a member of phytosterols and a 3beta-sterol. It has a role as a mouse metabolite. It derives from a hydride of a campestane.
Names & identifiers
- Preferred name
- Campesterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-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
CAMPESTEROL474-62-4Campesterin24(R)-methylcholesterolErgost-5-en-3-ol, (3beta,24R)-24alpha-MethylcholesterolErgost-5-en-3beta-ol, (24R)-delta5-24-Isoergosten-3beta-ol(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-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-ol5L5O665639CHEBI:28623DTXSID801009891
Show more names
Ergost-5-en-3-ol24α-methyl Cholesterol(24R)-Ergost-5-en-3β-olC01789CAMPESTROLMieyajunsu A-17-((2R,5R)
(3beta,24R)-ergost-5-en-3-olNSC-224330(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-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-olRefChem:31322DTXCID10209883 beta, 24R-ergost-5-en-3-ol207-484-4Campasterol
Database identifiers
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
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Oils and Extracts
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Ergosterols and C24-methyl derivatives [ST0103]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point157.5 °C
Physical Description
Solid; [Merck Index] White crystalline solid; [Sigma-Aldrich MSDS]
Solid
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
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Ergost-5-en-3-ol, (3.beta.,24R)-
Hazards Summary
Phytosterol esters containing 26-29% campesterol demonstrate no significant adverse effects in a 90-day oral study of rats; Phytosterol esters containing 27.9% campesterol produced decreased body weights, increased frequency of cardiomyopathy (males), and changes in hematology parameters in a 13-week oral study of rats at the highest tested dose (9,000 mg/kg/day); Phytosterol esters show no evidence of reproductive or developmental toxicity in rats; [JECFA] A moderate irritant; Harmful by ingestion, inhalation, and skin absorption; Targets the eyes, kidney, liver, and heart; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
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
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsExtracellular
Uses & manufacturing
UsesPresent in rape-seed oil, soybean oil, and wheat germ oil; [Merck Index] Added to food as a source of phytosterols (for blood cholesterol lowering properties); [JECFA]
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
Related reactions
1 records
Compound notes
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