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γ-sanshool

CAT: 0013-GTR19260333-01Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19260333-01Size:25 mg
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Description
γ-Sanshool can be isolated from Zanthoxylum piperitum. γ-Sanshool inhibits human ACAT-1 and ACAT-2 activities with IC50s of 12.0 and 82.6 μM.
CAS Number
78886-65-4
Purity
>98% (HPLC)
Solubility
DMSO : 50 mg/mL (182.88 mM; ultraphonic; )
Molecular Formula
C18H27NO
Molecular Weight
273.4131
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

gamma-Sanshool

Gamma-sanshool is an enamide obtained by the formal condensation of 2-methylpropanamine with tetradeca-2,4,8,10,12-pentaenoic acid (the 2E,4E,8Z,10E,12E stereoisomer). Isolated from Zanthoxylum piperitum, it exhibits inhibitory activity against acyl-CoA:cholesterol acyltransferase. It has a role as an EC 2.3.1.26 (sterol O-acyltransferase) inhibitor and a plant metabolite. It is a secondary carboxamide and an enamide. It is functionally related to a 2-methylpropanamine.

CAS Number78886-65-4
PubChem CID6440615
IUPAC Name(2E,4E,8Z,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide
Molecular FormulaC18H27NO
Molecular Weight273.4
XLogP4.9
Topological Polar Surface Area29.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count9
Heavy Atom Count20
Formal Charge0
Complexity384
SMILES
C/C=C/C=C/C=C\CC/C=C/C=C/C(=O)NCC(C)C
InChI
InChI=1S/C18H27NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-18(20)19-16-17(2)3/h4-9,12-15,17H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8-,13-12+,15-14+
InChIKey
KVUKDCFEXVWYBN-JDXPBYPHSA-N
Chemical Structure
2D Structure
2D structure of gamma-Sanshool
CAS: 78886-65-4
CID: 6440615
Formula: C18H27NO
MW: 273.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight273.4
XLogP34.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count9
Exact Mass273.209264485
Monoisotopic Mass273.209264485
Topological Polar Surface Area29.1 Ų
Heavy Atom Count20
Formal Charge0
Complexity384
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count5
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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AB2244Hydroxy-γ-sanshool
AB2243Hydroxy-β-sanshool
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