N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamid, (E)-

Capsaicin

HCID 1548943

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Grundinformationen

CAS: 404-86-4
Standard-SMILES: COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N
Summenformel: C18H27NO3
Durchschnittliche Molmasse: 305,418 g/mol
Monoisotopische Masse: 305,19909372

Namen und Bezeichner

Bevorzugter Name: Capsaicin
IUPAC: (6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Lokaler Name: N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamid, (E)-
Englischer Name: Capsaicin
Summenformel: C18H27NO3
Molmasse: 305.41

Namen und Synonyme

CAPSAICINEFEMA 2787QutenzaFEMA 3404Capsaicin(Vanilloid)TRANS-8-METHYL-N-VANILLYL-6-NONENAMIDEHaltTRANS-CAPSAICINCAPSAICINEXTRACTNatural Capsaicin

Datenbank-Bezeichner

CAS: 404-86-4
PubChem CID: 1548943
DTXSID: DTXSID9020241
ChEMBL: CHEMBL294199
ChEBI: CHEBI:3374
UNII: S07O44R1ZM
EC Number: 206-969-8
Nikkaji: J1.529F、J29.362H

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt: 62 · 62-65 °C(lit.)
Siedepunkt: 210 · 210-220 C
Dichte: 1.1037 · 1.1037 (rough estimate)
Brechungsindex: 1.51 · 1.5100 (estimate)
FEMA: 3404 · 3404 | CAPSAICIN
Flammpunkt: 113 °C · 113 °C
storage temp.: 2 · 2-8°C
Löslichkeit: 2 O: · H2O: insoluble
pka: 9.76 · 9.76±0.20(Predicted)
Aggregatzustand: Off-white solid
Farbe: Off-white
Geruch (Odor): mild warm herbal
Geruchsart: herbal
Biologische Quelle: Capsicum sp.
Wasserlöslichkeit: insoluble
Merck: 14 · 14,1768
BRN: 2816484 · 2816484
Henry's Law Constant: 9.9 · 9.9×107 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität: Stable. Incompatible with strong oxidizing agents.
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
Kosmetik-Inhaltsstoffe Funktionen: SKIN CONDITIONINGFRAGRANCE
InChI: 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+
InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N
SMILES: COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O
LogP: 4 · 4.00
CAS Datenbank: 404 · 404-86-4(CAS DataBase Reference)
EPA chemische Informationen: Capsaicin (404-86-4)

Sicherheit und Regulatorisches

Sicherheitsdaten

F: 10-21
wgk: 3
tsca: TSCA listed
ridadr: UN 2811 6.1/PG 2
hs_code: 29399990
RTECS-Nr.: RA8530000
risk_code: 25-37/38-41-42/43-36/37/38
Toxizität: LD50 oral in mouse: 47200ug/kg
hazard_code: T,T+
safety_code: 22-26-28-36/39-45-36/37/39
hazard_class: 6.1(a)
packing_group: II
Speicherklasse: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten: 404-86-4(Hazardous Substances Data)
Hazard Classifications: Acute Tox. 2 OralEye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungCapsaicin has a mild, warm-herbaceous odor and a burning pungent taste (at 10 ppm). It is used in compounded flavors for sauces where the pungent note is desired. This substance is present in several species of Capsicum (Family, Solanaceae). The sensation of pain, accompanied by irritation and inflammation, is due to substance P depletion from sensory (afferent) nerve fibers. These properties are used to study the physiology of pain and the effects as a counterirritant and gastrointestinal stimulant. This substance may be prepared from 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation form cis-capsaicin, pelargonic acid vanilamide, and dihydrocapsaicin, reaction of capsaicin.

OccurrenceThe pungent principle in the fruits of various Capsicum species (Solanaceae)

VerwendenCapsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.