Capsaicin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Capsaicin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Capsaicin?

The molecule Capsaicin presents a molecular formula of C18H27NO3 and its IUPAC name is (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide.

Capsaicin is the molecule responsible for the spicy heat in chili peppers. It is a natural product derived from the pepper plant, and its chemical structure was first determined in 1919. Capsaicin is an irritant to mammals, including humans, and produces a burning sensation upon contact. This sensation is caused by the activation of heat-sensitive neurons in the skin..

Capsaicin is used in pepper spray as a self-defense weapon and in topical ointments to provide relief from pain. It is also being studied for its potential health benefits, including its ability to fight cancer and obesity..

The spiciness of capsaicin is measured in Scoville heat units (SHU). The hottest chili peppers, such as the Carolina Reaper, can have a capsaicin concentration of up to 16 million SHU. In comparison, bell peppers have a capsaicin concentration of zero SHU..

Capsaicin is insoluble in water but can be extracted from peppers using an organic solvent such as ethanol. It is also possible to synthesize capsaicin in the laboratory..

Capsaicin has a number of potential health benefits. It is an antioxidant and has anti-inflammatory properties. Capsaicin also has the ability to boost metabolism and promote weight loss..

Some studies have shown that capsaicin can kill cancer cells and shrink tumors. It is also being studied as a treatment for pain, arthritis, and psoriasis..

Capsaicin is generally considered safe, but it can cause side effects such as skin irritation, stomach upset, and diarrhea. It is important to use capsaicin products as directed and to wash your hands after contact..

3D structure

Cartesian coordinates

Geometry of Capsaicin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Capsaicin YKPUWZUDDOIDPM-SOFGYWHQSA-N chemical compound 2D structure molecule svg
Capsaicin

 

Molecule descriptors

 
IUPAC name(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
InChI codeInChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChI KeyYKPUWZUDDOIDPM-SOFGYWHQSA-N
SMILESCOc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide #
  • (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
  • (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
  • (6E)-N-{[4-hydroxy-3-(methyloxy)phenyl]methyl}-8-methylnon-6-enamide
  • (E)-8-Methyl-N-vanillyl-6-nonenamide
  • (E)-8-Methyl-N-vanillyl-6-nonenamide(8cl)
  • (E)-Capsaicin
  • (E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide
  • (E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
  • (E)-N-[(4-Hydroxy-3-methoxyphenyl)-methyl]-8-methyl-6-nonenamide
  • (E)-N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-non-6-enamide
  • (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
  • (E)8-methyl-N-vanillyl-6-Nonenamide
  • (e)-n-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
  • 1217899-52-9
  • 404-86-4
  • 4DY
  • 6-Nonenamide, (E)-
  • 6-Nonenamide, (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl
  • 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-
  • 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (6E)-
  • 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
  • 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (6E)-
  • 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (E)-
  • 6-nonenamide,n-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-,(6e)-
  • 7553-53-9
  • 8-Methyl-N-Vanillyl-6-Nonenamide
  • 8-Methyl-N-vanillyl-(trans)-6-nonenamide
  • 8-Methyl-N-vanillyl-6-nonenamide, (E)-
  • 8-Methyl-N-vanillyl-6E-nonenamide
  • 8-Methyl-N-vanillyl-trans-6-nonenamide
  • AB00053098-11
  • AB00053098_12
  • AC-10114
  • ALGRX 4975
  • ALGRX-4975
  • AMY25669
  • Adlea
  • Ausanil
  • Axsain
  • BBL027836
  • BDBM20461
  • BDBM86537
  • BPBio1_001053
  • BRN 2816484
  • BSPBio_000957
  • BSPBio_001548
  • BSPBio_002917
  • C-1700
  • C06866
  • CAPSAICIN, NATURAL
  • CAPSAICINE
  • CAPSAICINOIDS
  • CAS_404-86-4
  • CCG-39657
  • CCG-39908
  • CCRIS 1588
  • CITRUS AURANTIUM PE
  • CS-0181240
  • CS-1518
  • Capsaicin
  • Capsaicin (8-Methyl-N-vanillyl-6-nonenamide)
  • Capsaicin (JAN/USP)
  • Capsaicin (Natural)
  • Capsaicin (in oleoresin of capsicum)
  • Capsaicin,(S)
  • Capsaicin; 8-Methyl-N-vanillyl-trans-6-nonenamide; NGX-4010
  • Capsaicinoid
  • Capsicine
  • Capzasin-hp
  • Caswell No. 158
  • Citrus Aurantium Extract
  • Cntx-4975
  • D00250
  • DB06774
  • DSSTox_CID_241
  • DSSTox_GSID_20241
  • DSSTox_RID_75455
  • Dolenon
  • E-CAPSAICIN
  • EI-125
  • EPA Pesticide Chemical Code 070701
  • FEMA No. 3404
  • GTPL2486
  • HMS1361N10
  • HMS1570P19
  • HMS1791N10
  • HMS1921H11
  • HMS1989N10
  • HMS2089N11
  • HMS2092D21
  • HMS2097P19
  • HMS2230O23
  • HMS3402N10
  • HMS3414F11
  • HMS3649N15
  • HMS3678F11
  • HMS501B16
  • HSDB 954
  • HY-10448
  • HY-10448A
  • IDI1_000354
  • IDI1_034018
  • Isodecenoate
  • Isodecenoic acid vanillylamide
  • KS-5181
  • LMFA08020085
  • LS-14673
  • M1149
  • MEGxp0_001448
  • MFCD00017259
  • MLS002154049
  • MR3H3
  • Methyl-N-vanillyl-6-noneneamide
  • Mioton
  • N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
  • N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)-
  • N-(3-Methoxy-4-hydroxybenzyl)-8-methyl-6-nonenamide
  • N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide
  • N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
  • N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
  • N-[(4-hydroxy-3-methoxyphenyl)methyl]-6E-8-methyl-nonenamide
  • N0C781
  • N1667
  • NCGC00017337-02
  • NCGC00017337-03
  • NCGC00017337-04
  • NCGC00017337-05
  • NCGC00017337-06
  • NCGC00017337-07
  • NCGC00017337-08
  • NCGC00017337-09
  • NCGC00017337-10
  • NCGC00017337-11
  • NCGC00017337-12
  • NCGC00017337-13
  • NCGC00017337-17
  • NCGC00017337-18
  • NCGC00090853-01
  • NCGC00090853-02
  • NCGC00090853-03
  • NCGC00090853-04
  • NCGC00090853-06
  • NCGC00090853-07
  • NCGC00090853-08
  • NCGC00090853-09
  • NCGC00090853-10
  • NCGC00090853-11
  • NCGC00090853-12
  • NCGC00257869-01
  • NCI-C56564
  • NGX 4010
  • NGX-1998
  • NGX-3781
  • NGX-4010
  • NGX-7325
  • NSC 56353
  • NSC-56353
  • NSC-757844
  • NSC56353
  • NSC757844
  • NSC_2548
  • Ovocap
  • Pharmakon1600-01501128
  • Prestwick2_000879
  • Prestwick3_000879
  • Prestwick_204
  • Q273169
  • Qutenza
  • Qutenza;Vanilloid
  • Ratden pe 40
  • S07O44R1ZM
  • SBI-0052593.P002
  • SDCCGMLS-0066678.P001
  • SMP2_000337
  • SMR000718774
  • SPECTRUM1501128
  • SR-05000001861
  • SR-05000001861-1
  • SR-05000001861-4
  • SR-05000001861-5
  • SR-05000001861-6
  • SR-05000001861-9
  • STL372889
  • Styptysat
  • TNP00277
  • TQ-1018
  • Togarashi orenji
  • Transacin
  • Vanilloid
  • Zostrix
  • Zostrix HP
  • capsacin(E)
  • depletes Substance P
  • epsilon-capsaicin
  • isoamyl4-methoxycinnamate
  • neurotoxic
  • s1990
  • starbld0019180
  • trans-8-Methyl-N-vanillyl-6-nonenamide
  • trans-Capsaicin
  • trans-Capsaicin-d3
  • trans-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530575
  • CAS-404-86-4
  • UNII-S07O44R1ZM
  • AKOS007930159
  • BRD-K37056290-001-01-1
  • BRD-K50590187-001-06-6
  • DTXSID9020241
  • CHEMBL294199
  • CHEBI:3374
  • CHEBI:94524
  • Tox21_110817
  • Tox21_200315
  • EINECS 206-969-8
  • UPCMLD-DP092
  • UPCMLD-DP092:001
  • UPCMLD-DP092:002
  • SCHEMBL8085
  • SCHEMBL8086
  • Spectrum5_000538

Physico-Chemical properties

IUPAC name(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Molecular formulaC18H27NO3
Molecular weight305.412
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity90.52
LogP4.2
Topological polar surface area58.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.