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Structure Database (LMSD)

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Common Name

Stigmasterol

Systematic Name

stigmasta-5,22E-dien-3β-ol

Synonyms

LM ID

LMST01040123

Formula

C₂₉H₄₈O

Exact Mass

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412.370516

Sum Composition

ST 29:2;O

Status

Curated

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Classification

Biological Context

Stigmasterol is a natural plant sterol that can be isolated from certain seed oils and herbs, including those used for therapeutic purposes.^1,2 Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration.^3,4,5 Alternatively, phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.⁶

This information has been provided by Cayman Chemical

References

1. Ali, H., Dixit, S., Ali, D., et al. Isolation and evaluation of anticancer efficacy of stigmasterol in a mouse model of DMBA-induced skin carcinoma. Drug. Des. Devel. Ther. 9, 2793-2800 (2015).

3. Ganie, S.A., and Yadav, S.S. Holoptelea integrifolia (Roxb.) Planch: A review of its ethnobotany, pharmacology, and phytochemistry. Biomed. Res. Int. 2014(401213), 1-12 (2014).

4. Mo, S., Dong, L., Hurst, J., et al. Quantitative analysis of phytosterols in edible oils using APCI liquid chromatography-tandem mass spectrometry. Lipids 48(9), 949-956 (2013).

5. Mutanen, A., Nissinen, M.J., Lohi, J., et al. Serum plant sterols, cholestanol, and cholesterol precursors associate with histological liver injury in pediatric onset intestinal failure. Am. J. Clin. Nutr. 100(4), 1085-1094 (2014).

2. Awad, A.B., and Fink, C.S. Phytosterols as anticancer dietary components: Evidence and mechanism of action. J. Nutr. 130, 2127-2130 (2000).

6. Tovey, F.I. Role of dietary phospholipids and phytosterols in protection against peptic ulceration as shown by experiments on rats. World J. Gastroenterol. 21(5), 1377-1384 (2015).

String Representations

InChiKey (Click to copy)

HCXVJBMSMIARIN-PHZDYDNGSA-N

InChi (Click to copy)

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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@@H](CC)C(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1