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Details

Stereochemistry ACHIRAL
Molecular Formula C18H29NO3
Molecular Weight 307.4278
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROCAPSAICIN

SMILES

COC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1

InChI

InChIKey=XJQPQKLURWNAAH-UHFFFAOYSA-N
InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)

HIDE SMILES / InChI
Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers. Like capsaicin, it contributes to the spicy taste of chili peppers, although it is less potent than capsacian. Dihydrocapsaicin has been shown to induce hypothermia in rats, a property which may help protect victims of stroke and cardiac arrest.

CNS Activity

Curator's Comment: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O35433
Gene ID: 83810.0
Gene Symbol: Trpv1
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Oxidative DNA damage by capsaicin and dihydrocapsaicin in the presence of Cu(II).
2001 Aug 28
Quantitative analysis of capsaicinoids in fresh peppers, oleoresin capsicum and pepper spray products.
2001 May
Antioxidant activity of capsinoids.
2002 Dec 4
Optimization of high-performance liquid chromatographic parameters for the determination of capsaicinoid compounds using the simplex method.
2002 Jun
Natural deuterium distribution in branched-chain medium-length fatty acids is nonstatistical: a site-specific study by quantitative 2H NMR spectroscopy of the fatty acids of capsaicinoids.
2002 Mar 1
Determination of capsaicinoids in topical cream by liquid-liquid extraction and liquid chromatography.
2002 Nov 7
Molecular mapping of capsaicinoid biosynthesis genes and quantitative trait loci analysis for capsaicinoid content in Capsicum.
2003 Dec
An alternative method to screen for pepper spray residue.
2003 Jan
Pharmacological effects of fermented red pepper.
2004 Nov
Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L).
2005 Mar 9
Toxicity and repellency of hot pepper extracts to spider mite, Tetranychus urticae Koch.
2006
Effects of capsaicin, dihydrocapsaicin, and curcumin on copper-induced oxidation of human serum lipids.
2006 Aug 23
Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin.
2006 Mar 30
QTL analysis for capsaicinoid content in Capsicum.
2006 Nov
Hot receptors in the brain.
2006 Nov 8
Effect of topical application of capsaicin and its related compounds on dermal insulin-like growth factor-I levels in mice and on facial skin elasticity in humans.
2007 Apr
Inheritance of capsaicin and dihydrocapsaicin, determined by HPLC-ESI/MS, in an intraspecific cross of Capsicum annuum L.
2007 Aug 22
Enzymatic synthesis of capsaicin analogs and their effect on the T-type Ca2+ channels.
2007 May 4
Separation of capsaicin from capsaicinoids by simulated moving bed chromatography.
2008 Apr 11
Ultrasound-assisted extraction of capsaicinoids from peppers.
2008 Jun 15
Dihydrocapsaicin (DHC), a saturated structural analog of capsaicin, induces autophagy in human cancer cells in a catalase-regulated manner.
2008 Nov
Analysis of capsaicin and dihydrocapsaicin in peppers and pepper sauces by solid phase microextraction-gas chromatography-mass spectrometry.
2009 Apr 3
Pungency in Capsicum chinense: variation among countries of origin.
2009 Feb
Impairment in function and expression of transient receptor potential vanilloid type 4 in Dahl salt-sensitive rats: significance and mechanism.
2010 Apr
Increased susceptibility to cardiovascular effects of dihydrocapcaicin in resuscitated rats. Cardiovascular effects of dihydrocapsaicin.
2010 Aug 31
Capsaicinoids in the hottest pepper Bhut Jolokia and its antioxidant and antiinflammatory activities.
2010 Jan
The unfolded protein response and its relevance to connective tissue diseases.
2010 Jan
Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo.
2012
Patents

Sample Use Guides

Twenty healthy subjects ingested a single dose of Capsimax capsaicinoid supplement after 12 hours of fasting. The supplement contains 100 mg of encapsulated beadlets, standardized to 2% capsaicinoids, of which 1.2-1.35% was capsaicin, 0.6-0.8% was dihydrocapsaicin, and 0.1-0.2% was nordihydrocapsaicin. Fasting blood samples were collected during each visit; 30 minutes following a rest period and before supplement intake (Pre); 2 hours post intake (2 hr); one minute following the cessation of 30 minutes of exercise performed at 65% of maximal heart rate reserve (2.5 hr); and 90 minutes following the cessation of exercise (4 hr). Heart rate (HR), systolic (SBP) and diastolic (DBP) blood pressure were recorded at all times. Blood glycerol was higher with Capsimax than for placebo at 4 hr and FFA was higher with Capsimax than for placebo at 2 hr.
Route of Administration: Oral
Human lung carcinoma cell line (A549) was maintained on DMEM supplemented with 9% heat-inactivated fetal bovine serum and 10 micro-g/mL gentamicin. The cells were grown at 37 deg-C in a 5% CO2 atmosphere. Cells were treated with increasing concentrations (100, 200, 300, and 400 micro-M) of dihydrocapsaicin dissolved in DMSO, fo 6, 12, 24, or 48 hours. After exposures, the culture mediums were collected and processed for metabolite analysis. The viability of cultured cells was determined by the MTT-reduction method. Dihydrocapsaicin decreased cell viability in a dose- and time-dependent way. The concentration corresponding to the EC50 was about 400 micro-M. The decrease in the viability by dihydrocapsaicin reached 50% within 6 hours.
Name Type Language
DIHYDROCAPSAICIN
USP-RS  
Common Name English
6,7-DIHYDROCAPSAICIN
Common Name English
NONANAMIDE, 8-METHYL-N-VANILLYL-
Systematic Name English
CAPSAICIN, DIHYDRO-
Common Name English
DIHYDROCAPSAICIN [USP-RS]
Common Name English
NONANAMIDE, N-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-8-METHYL-
Systematic Name English
DIHYDROCAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 70706
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
NCI_THESAURUS C68530
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
Code System Code Type Description
CAS
19408-84-5
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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RXCUI
2166037
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RS_ITEM_NUM
1200600
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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NCI_THESAURUS
C68531
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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WIKIPEDIA
DIHYDROCAPSAICIN
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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FDA UNII
W9BV32M08A
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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PUBCHEM
107982
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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MESH
C012906
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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CHEBI
46932
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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EPA CompTox
DTXSID4041864
Created by admin on Fri Dec 15 18:44:52 GMT 2023 , Edited by admin on Fri Dec 15 18:44:52 GMT 2023
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