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Safety Information

SML2232

Sigma-Aldrich

α-Spinasterol

≥98% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C29H48O
CAS Number:
481-18-5
Molecular Weight:
412.69
MDL number:
MFCD00200554
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Aster scaber

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

ethanol: 2 mg/mL, clear (warmed)

storage temp.

−20°C

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

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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.
α-Spinasterol is a constituent of argan oil. It regulates nuclear receptors expression and modulates mitochondrial function. It mimics natural cholesterol and its functionality. α-Spinastero lelicits cytoprotective and antiulcerogenic functionality. It has therapeutic potential towards diabetic nephropathy.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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The Potential of alpha-Spinasterol to Mimic the Membrane Properties of Natural Cholesterol
Haralampiev I, et al.
Molecules (Basel), 22(8), 1390-1390 (2017)
Evaluation of the antidepressant-and anxiolytic-like activity of alpha-spinasterol, a plant derivative with TRPV1 antagonistic effects, in mice
Socala K and Wlaz P
Behavioural Brain Research, 303, 19-25 (2016)
alpha-Spinasterol isolated from the root of Phytolacca americana and its pharmacological property on diabetic nephropathy
Jeong SI, et al.
Planta Medica, 70(08), 736-739 (2004)
Katarzyna Socała et al.
Journal of neural transmission (Vienna, Austria : 1996), 122(9), 1239-1247 (2015-03-13)
α-Spinasterol is a plant-derived compound which was reported to act as a selective antagonist for the transient receptor potential vanilloid 1 (TRPV1) receptor. Several studies revealed that the TRPV1 receptors might modulate seizure activity in animal models of seizures and

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