Structure via PubChem · Public domain (PubChem)
stigmasterol
Sign in to saveAlso known as (3beta,22E)-stigmasta-5,22-dien-3-ol, poriferasterol, 5,22-Cholestadien-24-ethyl-3beta-ol, stigmasta-5,22-dien-3beta-ol, beta-stigmasterol, (24S)-5,22-Stigmastadien-3beta-ol, Stigmasta-5,22-dien-3-beta-ol, Stigmasterin
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. 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.
Chemical data
- Formula
- C29H48O
- Molecular weight
- 412.7 g/mol
- IUPAC name
- (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
- InChIKey
- HCXVJBMSMIARIN-PHZDYDNGSA-N
- XLogP
- 8.6
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
3,294 papers- Stigmasterol Restores the Balance of Treg/Th17 Cells by Activating the Butyrate-PPARγ Axis in Colitis.Frontiers in immunology · 2021
- Stigmasterol alleviates neuropathic pain by reducing Schwann cell-macrophage cascade in DRG by modulating IL-34/CSF1R.CNS neuroscience & therapeutics · 2024
- Stigmasterol attenuates inflammatory response of microglia via NF-κB and NLRP3 signaling by AMPK activation.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
- Stigmasterol regulates microglial M1/M2 polarization via the TLR4/NF-κB pathway to alleviate neuropathic pain.Phytotherapy research : PTR · 2024
- Stigmasterol: An Enigmatic Plant Stress Sterol with Versatile Functions.International journal of molecular sciences · 2024
via PubMed
Wikidata facts
- Mass
- 412.370516
Show 4 more facts
- chemical formula
- C₂₉H₄₈O
- isomeric SMILES
- CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
- canonical SMILES
- CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
- Commons category
- Stigmasterol
via Wikidata · CC0
~3 min read
Article
7 sectionsContents
- Discovery
- Natural occurrences
- Uses
- Research
- Potential precursor of boldenone
- See also
- References
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. 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.
== Discovery ==