Chavicine

{{chembox

| Watchedfields = changed

| verifiedrevid = 399713250

| ImageFile=Chavicine.png

| ImageSize=

| PIN = (2Z,4Z)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

| OtherNames = (2Z,4Z)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 1265935

| InChI = 1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2-,7-3-

| InChIKey = MXXWOMGUGJBKIW-PORYWJCVBA

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2-,7-3-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MXXWOMGUGJBKIW-PORYWJCVSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=495-91-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 95JV386FPD

| PubChem=1548912

| SMILES = O=C(N1CCCCC1)\C=C/C=C\c2ccc3OCOc3c2

}}

|Section2={{Chembox Properties

| C=17 | H=19 | N=1 | O=3

| Appearance=

| Density= 1.211 g/mL

| MeltingPt=

| BoilingPtC=

| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

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Chavicine is a possibly pungent compound found in black pepper{{cite journal | doi = 10.1556/JPC.19.2006.3.16| title = Separation and identification of piperine and chavicine in black pepper by TLC and GC-MS| journal = Journal of Planar Chromatography: Modern TLC| volume = 19| issue = 109| pages = 250–252| year = 2006| last1 = Mărutoiu| first1 = Constantin| last2 = Gogoasa| first2 = Ioan| last3 = Oprean| first3 = Ioan| last4 = Mărutoiu| first4 = Olivia-Florena| last5 = Moise| first5 = Maria-Ioana| last6 = Tigae| first6 = Cristian| last7 = Rada| first7 = Maria| s2cid = 97700546}} and other species of the genus Piper. It is one of the four geometric isomers of piperine.

In light, especially ultra-violet light, chavicine is formed from its isomer piperine. Its flavor has been reported as flavorless{{cite journal |last1=De Cleyn |first1=R |last2=Verzele |first2=M |title=Constituents of peppers. I Qualitative Analysis of Piperine Isomers |journal=Chromatografia |date=1972 |volume=5 |pages=346–350 |doi=10.1007/BF02315254 |url=https://www.chm.bris.ac.uk/sillymolecules/chavicine.pdf |access-date=26 September 2023}}{{cite journal |last1=Tiwari |first1=Anshuly |last2=Mahadik |first2=Kakasaheb R. |last3=Gabhe |first3=Satish Y. |title=Piperine: A comprehensive review of methods of isolation, purification, and biological properties |journal=Medicine in Drug Discovery |date=2020 |volume=7 |page=100027 |doi=10.1016/j.medidd.2020.100027 |url=http://doi.org/10.1016/j.medidd.2020.100027 |access-date=26 September 2023|doi-access=free }} Chavicine will also re-isomerise back to piperine.{{cite journal |last1=Kozukue |first1=Nobuyuki |last2=Park |first2=Mal-Sun |last3=others |first3=and 5 |title=Kinetics of Light-Induced Cis−Trans Isomerization of Four Piperines and Their Levels in Ground Black Peppers as Determined by HPLC and LC/MS |journal=J. Agric. Food Chem. |date=2007 |volume=55 |issue=17 |pages=7131–7139 |doi=10.1021/jf070831p |pmid=17661483 |url=https://doi.org/10.1021/jf070831p |access-date=26 September 2023|url-access=subscription }}