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Chemical compound
Nordihydrocapsaicin
Names
Preferred IUPAC name
N -[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide
Other names
N -Vanillyl-7-methyloctanamide; Vanillylamide of 7-methyloctanoic acid; NDHC
Identifiers
ChemSpider
ECHA InfoCard
100.208.673
UNII
InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)
N Key: VQEONGKQWIFHMN-UHFFFAOYSA-N
N InChI=1/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)
Key: VQEONGKQWIFHMN-UHFFFAOYAS
CC(C)CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
C 17 H 27 N O 3
Molar mass
293.407 g·mol−1
Negligible
Solubility
Soluble in
DMSO ,
chloroform
Hazards
GHS labelling :
H300 ,
H315 ,
H319 ,
H335
P264 ,
P270 ,
P280 ,
P302+P352 ,
P305+P351+P338 ,
P321 ,
P330 ,
P362+P364 ,
P405 ,
P501
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Nordihydrocapsaicin Heat Above peak (pure Nordihydrocapsaicin is highly toxic )
Scoville scale 9,100,000
[1] SHU
Nordihydrocapsaicin is a capsaicinoid and analog and
congener of
capsaicin in
chili peppers (
Capsicum ).
Properties
Like capsaicin, it is an
irritant . Nordihydrocapsaicin accounts for about 7% of the total capsaicinoids mixture
[2] and has about half the pungency of capsaicin. Pure nordihydrocapsaicin is a
lipophilic colorless odorless crystalline to waxy solid. On the
Scoville scale it has 9,100,000 SHU (Scoville heat units ),
[1] significantly higher than pepper spray.
See also
References
^
a
b Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition . 29 (6): 435–474.
doi :
10.1080/10408399109527536 .
PMID
2039598 .
^ Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C : 442.
doi :
10.1039/j39680000442 .
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Acrolein
Allicin (
garlic )
Allyl isothiocyanate (
mustard ,
radish ,
horseradish ,
wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (
cannabis )
Cannabidiol (
cannabis )
Cannabigerol (
cannabis )
Cinnamaldehyde (
cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (
cumin )
Curcumin (
turmeric )
Dehydroligustilide (
celery )
Diallyl disulfide
Dicentrine (
Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (
ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (
celery ,
Angelica acutiloba )
Linalool (
Sichuan pepper ,
thyme )
Methylglyoxal
Methyl salicylate (
wintergreen )
N-Methylmaleimide
Nicotine (
tobacco )
Oleocanthal (
olive oil )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (
Dorrigo pepper )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tear gases
Tetrahydrocannabinol (
cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (
onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Allicin (
garlic )
AM404
Anandamide
Bisandrographolide (
Andrographis paniculata )
Camphor (
camphor laurel ,
rosemary ,
camphorweed ,
African blue basil ,
camphor basil )
Cannabidiol (
cannabis )
Cannabidivarin (
cannabis )
Capsaicin (
chili pepper )
Carvacrol (
oregano ,
thyme ,
pepperwort ,
wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (
chili pepper )
Estradiol
Eugenol (
basil ,
clove )
Evodiamine (
Euodia ruticarpa )
Gingerols (
ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (
chili pepper )
Homodihydrocapsaicin (
chili pepper )
Incensole (
incense )
Lysophosphatidic acid
Low
pH (acidic conditions)
Menthol (
mint )
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (
PAVA spray )
Nordihydrocapsaicin (
chili pepper )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g.,
4α-PDD )
Piperine (
black pepper ,
long pepper )
Polygodial (
Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (
Ruta graveolens )
Resiniferatoxin (RTX) (
Euphorbia resinifera /
pooissonii )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tetrahydrocannabivarin (
cannabis )
Thymol (
thyme ,
oregano )
Tinyatoxin (
Euphorbia resinifera /
pooissonii )
Tramadol
Vanillin (
vanilla )
Zucapsaicin
Blockers