Matricin

Matricin

Structure of matricin
Names
IUPAC name (11S)-4-Hydroxy-12-oxo-6α,12-epoxyguaia-1(10),2-dien-8α-yl acetate
Systematic IUPAC name (3S,3aR,4S,9R,9aS,9bS)-9-Hydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,9,9a,9b-octahydroazuleno[4,5-b]furan-4-yl acetate
Other names Proazulene; Prochamazulene
Identifiers
CAS Number	29041-35-8 checkY
3D model (JSmol)	Interactive image
ChemSpider	83299
ECHA InfoCard
EC Number	249-384-3
E number
PubChem CID	3483298
UNII	O034C3549S checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1 Key: SYTRJRUSWMMZLV-VQGWEXQJSA-N
SMILES C[C@H]1[C@@H]2[C@H](CC(=C3C=C[C@@]([C@@H]3[C@H]2OC1=O)(C)O)C)OC(=O)C
Properties
Chemical formula	C17H22O5
Molar mass	306.358 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Matricin is a colorless sesquiterpene found in the flowers of chamomille (Matricaria chamomilla). Steam distillation during the processing of chamomille can convert matricin to chamazulene, a blue-violet derivative of azulene. Oral ingestion of matricin results in chamazulene being found in blood plasma and artificial gastric fluid is able to convert matricin to chamazulene.

File:Chamazulen synthesis.png

Degradation of matricin (1) to chamazulene (3) via chamazulene carboxylic acid (2).