Basic information
- CAS
19408-84-5- Standard SMILES
COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O- InChIKey
XJQPQKLURWNAAH-UHFFFAOYSA-N- Molecular formula
- C18H29NO3
- Average molar mass
- 307.4 g/mol
- Monoisotopic mass
- 307.21474379
Overview
Dihydrocapsaicin is a capsaicinoid.
Names & identifiers
- Preferred name
- Dihydrocapsaicin
- IUPAC
- N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
- English name
- Dihydrocapsaicin
- Molecular formula
- C18H29NO3
- Molecular weight
- 307.43
Names & synonyms
Dihydrocapsaicin19408-84-56,7-Dihydrocapsaicin8-Methyl-N-vanillylnonanamideN-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamideNonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-Nonanamide, 8-methyl-N-vanillyl-W9BV32M08ADTXSID4041864CHEBI:46932N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamideNonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-
Show more names
CAPSAICINEN-(3-Methoxy-4-hydroxybenzyl)-8-methylnonanamide(E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDEFEMA 2787FEMA 3404CCRIS1589(E)-CAPSAICINihydrocapsaicinCAPSAICIN, NATURAL
N-[(4-Hydroxy-3-methoxy-phenyl)methyl]-8-methyl-nonanamideN-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl-nonanamideRefChem:34595DTXCID2021864606-308-7N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamidedihydro capsaicinDihydrocapsacine
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 58.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 10
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 307
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802]
Melting Point
65.5 - 65.8 °C
65.5-65.8 °F
Physical Description
Solid
Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is found in pepper (C. annum).
Collision Cross Section164.84 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 62 · 62-65 °C(lit.)
- Boiling point
- 497.4 · 497.4±35.0 °C(Predicted)
- Density
- 1.026 · 1.026±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 2 O: · H2O: insoluble
- pka
- 9.76 · 9.76±0.20(Predicted)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (97.6%)
Safety data
- F
- 10-21
- wgk
- 3
- rtecs
- RA8530000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29399990
- risk_code
- 25-37/38-41-42/43-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 22-26-28-36/39-45-36/37/39
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H301-H315-H319-H335
- Hazard Classifications
- Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionDihydrocapsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities. It is active against E. faecalis, B. subtilis, S. aureus, P. aeruginosa, K. pneumoniae, E. coli, and C. albicans (MICs = 0.6-10 μg/ml). Dihydrocapsaicin scavenges DPPH and ABTS radicals in cell-free assays. It increases LC3-II, a marker of autophagy, and catalase levels and reduces reactive oxygen species (ROS) production in normal WI38 lung fibroblasts and H1299, but not A549 or H460, lung cancer cells when used at a concentration of 200 μM. Dihydrocapsaicin is an agonist of transient receptor potential vanilloid 1 (TRPV1) and inhibits NETosis induced by phorbol 12-myristate 13-acetate (TPA; ) in isolated human neutrophils. It induces cortical and systemic hypothermia and reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 0.5 mg/kg, i.p.
UsesDihydrocapsaicin has been used as a reference standard for the identification of dihydrocapsaicin in blood and tissue samples by high performance liquid chromatography (HPLC) combined with tandem mass spectrometry (MS) and in tomato-based salsas by enzyme immunoassay (EIA) and LC with fluorescent detection. It may be used as a reference standard for the determination of dihydrocapsaicin in Capsicum fruit samples by HPLC equipped with a Surveyor photodiode array (PDA) detector and in rat plasma by HPLC-triple quadrupole MS with electrospray ionization (ESI) in selected reaction monitoring (SRM) mode.
UsesCapsaicin (C175680) analog. A VR1 vaniloid receptor agonist.
General DescriptionDihydrocapsaicin belongs to the capsaicinoid group of compounds which are responsible for the pungency of capsicum fruits.
Suppliers100 total
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Related reactions
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Compound notes
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