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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

Molecular Formula C18H29NO3
Molecular Weight 307.4278
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo.
2012
Rapid method for the determination of capsaicin and dihydrocapsaicin in Gochujang using ultra-high-performance liquid chromatography.
2011-02-15
[Simultaneously determination of atropine sulphate, diphenhydramine hydrochloride, capsaicin and dihydrocapsaicin in pain-relieving plaster for arthritis by RP-HPLC].
2010-11
Drug-induced mild therapeutic hypothermia obtained by administration of a transient receptor potential vanilloid type 1 agonist.
2010-10-09
Effects of dihydrocapsiate on adaptive and diet-induced thermogenesis with a high protein very low calorie diet: a randomized control trial.
2010-10-06
Increased susceptibility to cardiovascular effects of dihydrocapcaicin in resuscitated rats. Cardiovascular effects of dihydrocapsaicin.
2010-08-31
Simultaneous quantification of capsaicin and dihydrocapsaicin in rat plasma using HPLC coupled with tandem mass spectrometry.
2010-08-15
Effect of oral intake of capsaicinoid beadlets on catecholamine secretion and blood markers of lipolysis in healthy adults: a randomized, placebo controlled, double-blind, cross-over study.
2010-07-15
Selective induction of catalase-mediated autophagy by dihydrocapsaicin in lung cell lines.
2010-07-15
Growth, yield, and fruit quality of pepper plants amended with two sanitized sewage sludges.
2010-06-09
Impairment in function and expression of transient receptor potential vanilloid type 4 in Dahl salt-sensitive rats: significance and mechanism.
2010-04
Capsaicinoids in the hottest pepper Bhut Jolokia and its antioxidant and antiinflammatory activities.
2010-01
The unfolded protein response and its relevance to connective tissue diseases.
2010-01
Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers.
2010
Effect of capsaicin and dihydrocapsaicin on in vitro blood coagulation and platelet aggregation.
2009-12
Preparative separation of capsaicin and dihydrocapsaicin from Capsicum frutescens by high-speed counter-current chromatography.
2009-09
Acute effects of dihydrocapsaicin and capsaicin on the distribution of white blood cells in rats.
2009-06
Interdisciplinary review for correlation between the plant origin capsaicinoids, non-steroidal antiinflammatory drugs, gastrointestinal mucosal damage and prevention in animals and human beings.
2009-06
Analysis of capsaicin and dihydrocapsaicin in peppers and pepper sauces by solid phase microextraction-gas chromatography-mass spectrometry.
2009-04-03
Vanilloid-mediated apoptosis in prostate cancer cells through a TRPV-1 dependent and a TRPV-1-independent mechanism.
2009-04
Endoplasmic reticulum stress-mediated autophagy/apoptosis induced by capsaicin (8-methyl-N-vanillyl-6-nonenamide) and dihydrocapsaicin is regulated by the extent of c-Jun NH2-terminal kinase/extracellular signal-regulated kinase activation in WI38 lung epithelial fibroblast cells.
2009-04
Pungency in Capsicum chinense: variation among countries of origin.
2009-02
Mobility of heavy metals from soil into hot pepper fruits: a field study.
2009-01
Dihydrocapsaicin (DHC), a saturated structural analog of capsaicin, induces autophagy in human cancer cells in a catalase-regulated manner.
2008-11
Ultrasound-assisted extraction of capsaicinoids from peppers.
2008-06-15
[Preparation of three capsaicinoid components using preparative high performance liquid chromatography].
2008-05
Separation of capsaicin from capsaicinoids by simulated moving bed chromatography.
2008-04-11
In vitro hepatic and skin metabolism of capsaicin.
2008-04
Herbal compounds and toxins modulating TRP channels.
2008-03
Inheritance of capsaicin and dihydrocapsaicin, determined by HPLC-ESI/MS, in an intraspecific cross of Capsicum annuum L.
2007-08-22
Determination of capsaicinoids in habanero peppers by chemometric analysis of UV spectral data.
2007-07-25
Growing hot pepper for cabbage looper, Trichopulsia ni (Hübner) and spider mite, Tetranychus urticae (Koch) control.
2007-06-15
Enzymatic synthesis of capsaicin analogs and their effect on the T-type Ca2+ channels.
2007-05-04
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.
2007-04
Determination of capsaicin and dihydrocapsaicin in capsicum fruits by liquid chromatography-electrospray/time-of-flight mass spectrometry.
2006-12-13
Hot receptors in the brain.
2006-11-08
QTL analysis for capsaicinoid content in Capsicum.
2006-11
Determination of capsaicinoids in peppers by microwave-assisted extraction-high-performance liquid chromatography with fluorescence detection.
2006-09-25
Effects of capsaicin, dihydrocapsaicin, and curcumin on copper-induced oxidation of human serum lipids.
2006-08-23
Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits.
2006-08-09
Pressurized liquid extraction of capsaicinoids from peppers.
2006-05-03
Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin.
2006-03-30
Toxicity and repellency of hot pepper extracts to spider mite, Tetranychus urticae Koch.
2006
Screening Capsicum accessions for capsaicinoids content.
2006
Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry.
2005-11-16
Extraction of capsaicins in aerosol defense sprays from fabrics.
2005-08-15
Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry.
2005-04
Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L).
2005-03-09
Pharmacological effects of fermented red pepper.
2004-11
Monomeric C18 chromatographic method for the liquid chromatographic determination of lipophilic antioxidants in plants.
2004-09-10
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:20:10 GMT 2025
Edited
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on Mon Mar 31 19:20:10 GMT 2025
Record UNII
W9BV32M08A
Record Status Validated (UNII)
Record Version
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Name Type Language
DIHYDROCAPSAICIN
USP-RS  
Common Name English
6,7-DIHYDROCAPSAICIN
Preferred 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 Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
NCI_THESAURUS C68530
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
Code System Code Type Description
CAS
19408-84-5
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
RXCUI
2166037
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
RS_ITEM_NUM
1200600
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
NCI_THESAURUS
C68531
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
WIKIPEDIA
DIHYDROCAPSAICIN
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
FDA UNII
W9BV32M08A
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
PUBCHEM
107982
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
MESH
C012906
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
CHEBI
46932
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID4041864
Created by admin on Mon Mar 31 19:20:11 GMT 2025 , Edited by admin on Mon Mar 31 19:20:11 GMT 2025
PRIMARY
Related Record Type Details
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PARENT -> CONSTITUENT ALWAYS PRESENT
36% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
36% of Capsaicinoid components.
TARGET -> AGONIST
16,000,000 Scoville units same as Capsaicin
PARENT -> CONSTITUENT ALWAYS PRESENT
36% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
36% of Capsaicinoid components.