Structure via PubChem · Public domain (PubChem)
nonivamide
Sign in to saveAlso known as hydroxymethoxybenzyl pelargonamide, vanillyl-N-nonylamide, N-nonanoyl vanillylamide, N-vanillylnonamide, N-vanillylpelargonamide, pelargonyl vanillylamide, pseudocapsaicin
Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.
Key facts
- Pepper.heat
- Above peak
- Pepper.scoville
- 9,200,000
via Wikipedia infobox
Chemical data
- Formula
- C17H27NO3
- Molecular weight
- 293.4 g/mol
- IUPAC name
- N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
- SMILES
- CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
- InChIKey
- RGOVYLWUIBMPGK-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 58.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- Low back pain
via ChEMBL · EBI
Research
131 papers- Nonivamide induces brown fat-like characteristics in porcine subcutaneous adipocytes.Biochemical and biophysical research communications · 2022
- Nonivamide inhibits proliferation of human corneal epithelial cells by inducing cell cycle arrest and oxidative stress.Toxicology · 2023
- Production of capsaicinoid nonivamide from plant oil and vanillylamine via whole-cell biotransformation.Bioresource technology · 2023
- No Influence of Nonivamide-nicoboxil on the Peak Power Output in Competitive Sportsmen.International journal of sports medicine · 2021
- Recent Progress on Capsaicin- and Nonivamide-Type Compounds as Agrochemicals and Drugs.Journal of agricultural and food chemistry · 2026
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 293.199
Show 5 more facts
- chemical formula
- C₁₇H₂₇NO₃
- canonical SMILES
- CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
- isomeric SMILES
- CCCCCCCC/C(=N/CC1=CC=C(C(=C1)OC)O)/O
- Scoville grade
- 9200000
- found in taxon
- Capsicum annuum
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Treatment
- See also
- References
Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.
Nonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionery industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin.
Excerpted from Wikipedia’s “nonivamide” article, available under the CC BY-SA 4.0 licence.