Stigmasterol

Names

[ CAS No. ]:
83-48-7

[ Name ]:
Stigmasterol

[Synonym ]:
(24S)-5,22-Stigmastadien-3b-ol
Stigmasta-5,22-dien-3-ol, (3β,22E)-
STIGMASTEROL (STIGMASTERIN)
(24S)-Stigmast-5,22-dien-3β-ol
STIGMASTEROL(P)
Wulzen anti-stiffness factor
Guinea-pig-anti-stiffness factor
SULFISOXAZOLE
Stigmasta-5,22-dien-3-ol, (3β,22E)- (9CI)
Stigmasta-5,22-dien-3β-ol
Stigmasterol
δ5,22-Stigmastadien-3β-ol
Anti-stiffness factor
(3β,22E)-Stigmasta-5,22-dien-3-ol
Stigmasta-5,22-dien-3-ol, (3β)-
Stigmasta-5,22-dien-3-ol, (3β,20R,22E,24S)-
MFCD00003630
Stigmasta-5,22-dien-3β-ol (8CI)
Stigmasta-5,22E-dien-3β-ol
isofucosterol
stigmasta-5,22-dien-3-b-ol
Stigmastero
STIGMASTA-5,22-DIEN-3-OL,(3B,22E)-
EINECS 201-482-7
Stigmasterin
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,3E,5S)-5-Ethyl-6-methyl-3-hepten-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
(3β,20R,22E,24S)-Stigmasta-5,22-dien-3-ol
3b-Hydroxy-24-ethyl-D5,22-cholestadiene
δ5-Stigmasterol
24S-ethylcholest-5,22-dien-3β-ol
stigmasta-5,22-dien-3-β-ol
β-Stigmasterol
(24S)-5,22-Stigmastadien-3β-ol
(3b,22E)-Stigmasta-5,22-dien-3-ol
5,22-stigmastadien-3β-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-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
PHYTOSTEROL
UNII-99WUK5D0Y8
(24S)-24-Ethylcholesta-5,22-dien-3β-ol

Biological Activity

[Description]:

Stigmasterol is a plant sterol which has been focused on the cholesterol-lowering activity and is valued as an anti-stiffness factor in the therapy of rheumatic diseases.

[Related Catalog]:

Natural Products >> Steroids

Research Areas >> Inflammation/Immunology

[Target]

MMP[1]

[In Vitro]

Preincubation of Stigmasterol to IL-1beta-treated cells shows signiﬁcant reduction of MMP-3 mRNA in human and mouse, MMP-3 protein in mouse, MMP-13 mRNA in mouse and human, ADAMTS-4 mRNA in human, PGE2 protein in human and mouse. Stigmasterol is also capable of counteracting the IL-1beta-induced NF-κB pathway[1].

[Cell Assay]

A model of newborn mouse chondrocytes and human osteoarthritis (OA) chondrocytes are used in primary culture stimulated with or without IL-1β (10 ng/mL), for 18 h. Cells are pre-incubated with Stigmasterol (20 mg/mL) for 48 h[1].

[References]

[1]. Gabay O, et al. Stigmasterol: a phytosterol with potential anti-osteoarthritic properties. Osteoarthritis Cartilage. 2010 Jan;18(1):106-16.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
501.1±19.0 °C at 760 mmHg

[ Melting Point ]:
165-167 °C(lit.)

[ Molecular Formula ]:
C₂₉H₄₈O

[ Molecular Weight ]:
412.691

[ Flash Point ]:
219.4±13.7 °C

[ Exact Mass ]:
412.370514

[ PSA ]:
20.23000

[ LogP ]:
10.21

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.531

[ Storage condition ]:
2~8°C

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H319-H331-H336-H351-H361d-H372

[ Precautionary Statements ]:
P201-P261-P304 + P340 + P312-P305 + P351 + P338-P308 + P313-P403 + P233

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn,Xi

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25-S36/37

[ RIDADR ]:
UN 1888 6.1/PG 3

[ WGK Germany ]:
3

[ HS Code ]:
2906199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2906199090

[ Summary ]:
2906199090. cyclanic, cyclenic or cyclotherpenic alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

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