Stigmasterol

Stigmasterol
Ball-and-stick model of stigmasterol
Names
IUPAC name
Stigmasta-5,22-dien-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,3E,5S)-5-Ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Other names
Stigmasterin; Wulzen anti-stiffness factor
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.348 Edit this at Wikidata
UNII
  • 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 checkY
    Key: HCXVJBMSMIARIN-PHZDYDNGSA-N checkY
  • InChI=1/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
    Key: HCXVJBMSMIARIN-PHZDYDNGBL
  • CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
Properties
C29H48O
Molar mass 412.702 g·mol−1
Appearance White solid[1]
Melting point 160 to 164 °C (320 to 327 °F; 433 to 437 K)[1]
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Stigmasterol – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes.[2] In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.[3]

  1. ^ a b Stigmasterol, ChemicalLand21.com
  2. ^ Ferrer A, Altabella T, Arró M, Boronat A (July 2017). "Emerging roles for conjugated sterols in plants". Progress in Lipid Research. 67: 27–37. doi:10.1016/j.plipres.2017.06.002. hdl:2445/118729. PMID 28666916.
  3. ^ Cabral CE, Klein MR (November 2017). "Phytosterols in the Treatment of Hypercholesterolemia and Prevention of Cardiovascular Diseases". Arquivos Brasileiros de Cardiologia. 109 (5): 475–482. doi:10.5935/abc.20170158. PMC 5729784. PMID 29267628.