cis-Capsaicin

• CAT Number: R052317
• CAS Number: 25775-90-0
• Molecular Formula: C18H27NO3
• Molecular Weight: 305.42
• Purity: ≥95%
• Synonyms: (6Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide; (Z)-8-Methyl-N-vanillyl-6-nonenamide; (Z)-8-Methyl-N-vanillyl-6-nonenamide; (Z)-Capsaicin; Civamide; Zucapsaicin
• Target: Neuronal Signaling
• Storage: Desiccate at RT
• IUPAC Name: (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-
• InChIKey: YKPUWZUDDOIDPM-VURMDHGXSA-N
• SMILES: CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

cis-Capsaicin is a naturally occurring structural isomer of capsaicin, the active compound in chili peppers. It selectively activates the TRPV1 (transient receptor potential vanilloid 1) ion channel, inducing calcium influx and triggering pain and heat sensations. Although less potent than the trans-isomer, cis-Capsaicin is valuable in studies of pain modulation, sensory neuron function, and thermoregulation. Its role in inflammation, analgesia, and metabolic regulation makes it a critical tool in pharmacological and physiological research focused on nociception and TRPV1-targeted therapies.