Description
Stigmasterol · CAS 83-48-7 · C29H48O. UNII 99WUK5D0Y8. Melting Point: 170 °C.
Identification
| CAS Registry Number | 83-48-7 |
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| PubChem CID | 5280794 |
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| Molecular formula | C29H48O |
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| IUPAC name | (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
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| UNII (FDA) | 99WUK5D0Y8 |
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Computed Descriptors
| Molecular Weight | 412.7 |
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| XLogP3 | 8.6 |
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| Hydrogen Bond Donor Count | 1 |
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| Hydrogen Bond Acceptor Count | 1 |
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| Rotatable Bond Count | 5 |
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| Exact Mass | 412.370516150 |
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| Monoisotopic Mass | 412.370516150 |
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| Topological Polar Surface Area | 20.2 |
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| Heavy Atom Count | 30 |
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| Formal Charge | 0 |
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Physical & Chemical Properties
Physical description & handling notes
- Solid
- Very soluble in benzene, ethyl ether, ethanol
- Soluble in the usual organic solvents
- Crystals from alcohol. When dry, mp 170 °C. Specific optical rotation: -51 deg at 22 °C/D ( c = 2 in chloroform). Insoluble in water. Soluble in the usual organic solvents /Monohydrate/
- 203.09 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
- MP: 144 °C. Specific optical rotation: -55.6 deg( c = 2 in chloroform) /Acetate/
Regulatory Status
| GHS notification summary | 50% (2 / 4) |
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GHS Hazard Classification
| GHS notification summary | 50% (2 / 4) |
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| Reported hazard statements | H302 (25%), H312 (25%), H315 (25%), H319 (25%), H332 (25%), H335 (25%), H413 (25%) |
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This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.
H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
Documented Uses
- Preparation of progesterone and other important steroids
- Usually isolated from the phytosterol mixture from soy or calabar beans
- Stigmasterol occurs with beta-sitosterol at a concentration of 12-25% in the nonsaponifiable fraction of soybean oil. The sterols are extracted as a mixture, but their similarity makes the purification and isolation of stigmasterol extremely difficult.
- Rats were dosed by oral gavage with 14C-labelled samples of cholesterol, beta-sitosterol or beta-sitostanol or (3)H-labelled samples of beta-sitostanol, campesterol, campestanol or stigmasterol dissolved in sunflower seed oil. Urine and feces were collected for up to 96 hours after dosing. ... Animals were sacrificed and either prepared for whole body autoradiography or tissues and carcass remains were assayed for 14C or (3)H. The overall absorption of phytosterols was low as judged by tissue and carcass levels of
- Intestinal absorption of cholesterol, campesterol, campestanol, stigmasterol and sitosterol were measured in 10 healthy subjects by an intestinal perfusion technique over a 50 cm segment of the upper jejunum using sitostanol as non-absorbable marker. Cholesterol absorption was highest and averaged 33%., whereas the absorption rate of sitosterol averaged 4.2% and of stigmasterol 4.8%....
- To study the effects of dietary stigmasterol on sterol and bile acids metabolism, Wistar rats were fed diets containing various amounts of stigmasterol. Feeding high stigmasterol doses (11, 26 or 52 mg/day) led to increased cholesterol, coprostanol and bile acid output. These effects were dose-dependent, and likely to be related to the inhibitory effect of plant sterols on cholesterol absorption. Moreover, it accounts for the beneficial effect of the stigmasterol on cholesterol lowering.
Synonyms
STIGMASTEROL; 83-48-7; Stigmasterin; beta-Stigmasterol; (24S)-5,22-Stigmastadien-3beta-ol; Stigmasta-5,22-dien-3beta-ol; 99WUK5D0Y8; (3beta,22E)-Stigmasta-5,22-dien-3-ol; NSC-8095; Stigmasta-5,22-dien-3-ol, (3beta,22E)-; Stigmasta-5,22-dien-3-ol, (3beta)-; CHEBI:28824; DTXSID801015733; RefChem:6262; DTXCID601473919; 201-482-7
Frequently Asked Questions
What are the CAS number and molecular formula of Stigmasterol?
CAS 83-48-7; molecular formula C29H48O; molecular weight — g/mol.
What other names is Stigmasterol known by?
STIGMASTEROL, 83-48-7, Stigmasterin, beta-Stigmasterol, (24S)-5,22-Stigmastadien-3beta-ol, Stigmasta-5,22-dien-3beta-ol.
Is Stigmasterol classified as hazardous?
50% of GHS notifications report no hazard classification (2 of 4).
What are the key physical properties of Stigmasterol?
Melting Point: 170 °C.
Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.
