PHL85776

α-Spinasterol

phyproof^® Reference Substance

• Synonym(s): α-Spinasterin, (3β,5α,22E)-Stigmasta-7,22-dien-3-ol, (E)-5α-Stigmasta-7,22-dien-3β-ol, 5α-Stigmasta-7,22-dien-3β-ol, Bessisterol, Hitodesterol, Spinasterol
• Empirical Formula (Hill Notation): C₂₉H₄₈O
• CAS Number: 481-18-5
• Molecular Weight: 412.69
• MDL number: MFCD00200554
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: primary reference standard
• product line: phyproof^® Reference Substance
• assay: ≥90.0% (HPLC)
• form: solid
• manufacturer/tradename: PhytoLab
• SMILES string: C[C@@]12[C@](CC[C@]2([H])[C@H](C)/C=C/[C@@H](CC)C(C)C)([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC1
• InChI: 1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3/b9-8+/t20-,21-,22+,23+,25-,26+,27+,28+,29-/m1/s1
• InChI key: JZVFJDZBLUFKCA-FXIAWGAOSA-N

Description

General description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

α-Spinasterol is a blood-brain barrier-permeable and orally active plant phytosterol with antioxidant, anticonvulsant (0.1-1 mg/kg i.p. in mice), antidepressant (1-2 mg/kg i.p. in mice) and anti-inflammatory (0.001-1 mg/kg, i.p. or 1-10 mg/kg, i.g. in mice) properties, as well as antinociceptive efficacy via dual actions against transient receptor potential vanilloid 1 (TrpV1; IC50/Emax = 1.4 μM/67% against 2 nM RTX for binding mouse spinal cord membranes; IC50/Emax = 40 μM/62% against 20 μM capsaicin-induced mouse spinal cord synaptosomes Ca2+ influx) and cyclooxygenases (IC50 = 16.17 μM/COX1 and 7.76μM/COX2). a-spinasterol can directly affect membrane structure and packing in a manner similar to cholesterol, both a-spinasterol and stitosterol are reported to lower plasma/liver cholesterol levels and increase fecal cholesterol excretion when supplemented in daily diet (1%) in mice in vivo.

Other Notes

This compound is commonly found in plants of the genus: hedera

Legal Information

phyproof is a registered trademark of PhytoLab GmbH & Co. KG

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable