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Details

Stereochemistry ACHIRAL
Molecular Formula C18H29NO3
Molecular Weight 307.4284
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROCAPSAICIN

SMILES

CC(C)CCCCCCC(=NCc1ccc(c(c1)OC)O)O

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 307.4284
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

PubMed

PubMed

TitleDatePubMed
Pharmacological effects of fermented red pepper.
2004 Nov
Monomeric C18 chromatographic method for the liquid chromatographic determination of lipophilic antioxidants in plants.
2004 Sep 10
Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry.
2005 Apr
Extraction of capsaicins in aerosol defense sprays from fabrics.
2005 Aug 15
Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L).
2005 Mar 9
Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry.
2005 Nov 16
Toxicity and repellency of hot pepper extracts to spider mite, Tetranychus urticae Koch.
2006
Screening Capsicum accessions for capsaicinoids content.
2006
Effects of capsaicin, dihydrocapsaicin, and curcumin on copper-induced oxidation of human serum lipids.
2006 Aug 23
Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits.
2006 Aug 9
Determination of capsaicin and dihydrocapsaicin in capsicum fruits by liquid chromatography-electrospray/time-of-flight mass spectrometry.
2006 Dec 13
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
Pressurized liquid extraction of capsaicinoids from peppers.
2006 May 3
QTL analysis for capsaicinoid content in Capsicum.
2006 Nov
Hot receptors in the brain.
2006 Nov 8
Determination of capsaicinoids in peppers by microwave-assisted extraction-high-performance liquid chromatography with fluorescence detection.
2006 Sep 25
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
Determination of capsaicinoids in habanero peppers by chemometric analysis of UV spectral data.
2007 Jul 25
Growing hot pepper for cabbage looper, Trichopulsia ni (Hübner) and spider mite, Tetranychus urticae (Koch) control.
2007 Jun-Jul
Enzymatic synthesis of capsaicin analogs and their effect on the T-type Ca2+ channels.
2007 May 4
In vitro hepatic and skin metabolism of capsaicin.
2008 Apr
Separation of capsaicin from capsaicinoids by simulated moving bed chromatography.
2008 Apr 11
Ultrasound-assisted extraction of capsaicinoids from peppers.
2008 Jun 15
Herbal compounds and toxins modulating TRP channels.
2008 Mar
[Preparation of three capsaicinoid components using preparative high performance liquid chromatography].
2008 May
Dihydrocapsaicin (DHC), a saturated structural analog of capsaicin, induces autophagy in human cancer cells in a catalase-regulated manner.
2008 Nov
Vanilloid-mediated apoptosis in prostate cancer cells through a TRPV-1 dependent and a TRPV-1-independent mechanism.
2009 Apr
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 Apr
Analysis of capsaicin and dihydrocapsaicin in peppers and pepper sauces by solid phase microextraction-gas chromatography-mass spectrometry.
2009 Apr 3
Effect of capsaicin and dihydrocapsaicin on in vitro blood coagulation and platelet aggregation.
2009 Dec
Pungency in Capsicum chinense: variation among countries of origin.
2009 Feb
Mobility of heavy metals from soil into hot pepper fruits: a field study.
2009 Jan
Acute effects of dihydrocapsaicin and capsaicin on the distribution of white blood cells in rats.
2009 Jun
Interdisciplinary review for correlation between the plant origin capsaicinoids, non-steroidal antiinflammatory drugs, gastrointestinal mucosal damage and prevention in animals and human beings.
2009 Jun
Preparative separation of capsaicin and dihydrocapsaicin from Capsicum frutescens by high-speed counter-current chromatography.
2009 Sep
Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers.
2010
Impairment in function and expression of transient receptor potential vanilloid type 4 in Dahl salt-sensitive rats: significance and mechanism.
2010 Apr
Simultaneous quantification of capsaicin and dihydrocapsaicin in rat plasma using HPLC coupled with tandem mass spectrometry.
2010 Aug 15
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
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 Jul 15
Selective induction of catalase-mediated autophagy by dihydrocapsaicin in lung cell lines.
2010 Jul 15
Growth, yield, and fruit quality of pepper plants amended with two sanitized sewage sludges.
2010 Jun 9
[Simultaneously determination of atropine sulphate, diphenhydramine hydrochloride, capsaicin and dihydrocapsaicin in pain-relieving plaster for arthritis by RP-HPLC].
2010 Nov
Rapid method for the determination of capsaicin and dihydrocapsaicin in Gochujang using ultra-high-performance liquid chromatography.
2010 Nov-Dec
Effects of dihydrocapsiate on adaptive and diet-induced thermogenesis with a high protein very low calorie diet: a randomized control trial.
2010 Oct 6
Drug-induced mild therapeutic hypothermia obtained by administration of a transient receptor potential vanilloid type 1 agonist.
2010 Oct 9
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:09:22 UTC 2021
Edited
by admin
on Sat Jun 26 00:09:22 UTC 2021
Record UNII
W9BV32M08A
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
NCI_THESAURUS C68530
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
Code System Code Type Description
CAS
19408-84-5
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
USP_CATALOG
1200600
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY USP-RS
RXCUI
2166037
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
NCI_THESAURUS
C68531
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
WIKIPEDIA
DIHYDROCAPSAICIN
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
FDA UNII
W9BV32M08A
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
PUBCHEM
107982
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
MESH
C012906
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
EPA CompTox
19408-84-5
Created by admin on Sat Jun 26 00:09:23 UTC 2021 , Edited by admin on Sat Jun 26 00:09:23 UTC 2021
PRIMARY
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36% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
36% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
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PARENT -> CONSTITUENT ALWAYS PRESENT
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