| Identification | Back Directory | [Name]
(4R)-4-(3-Oxo-1-buten-1-ylidene)-3α,5,5-trimethylcyclohexane-1α,3β-diol | [CAS]
41703-38-2 | [Synonyms]
Grasshopper ketone
(4R)-4-(3-Oxo-1-buten-1-ylidene)-3α,5,5-trimethylcyclohexane-1α,3β-diol
3-Buten-2-one, 4-[(1S,2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-, (3S)- | [Molecular Formula]
C13H20O3 | [MOL File]
41703-38-2.mol | [Molecular Weight]
224.3 |
| Hazard Information | Back Directory | [Uses]
It is a bioactive compound with anti-inflammatory activity that inhibits LPS-induced NO production in RAW 264.7 cells and acts by inhibiting the phosphorylation of MAPK (ERK, JNK and p38) and NF-κB p65. Grasshopper ketone, as an ingredient, has shown its potential in anti-inflammatory inhibition[1]. | [Definition]
ChEBI: Grasshopper ketone is a member of the class of allenes that is cyclohexane substituted by 3-oxobut-1-en-1-ylidene, methyl, hydroxy, hydroxy, methyl and methyl groups at positions 1, 2, 2, 4, 6 and 6, respectively (the 2R,3R,4S-stereoisomer). It is isolated from the grasshopper, Romalea microptera. It has a role as a phytotoxin, a plant metabolite, an algal metabolite, an anti-inflammatory agent, a marine metabolite and an animal metabolite. It is a tertiary allylic alcohol, a member of cyclohexanols, a diol, a methyl ketone, a secondary alcohol, an enone and a member of allenes. | [References]
[1] [Chemical constituents of Physalis minima] DOI:10.19540/j.cnki.cjcmm.20210525.202 |
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