Hirsutidin
Names
IUPAC name
3,4′,5-Trihydroxy-3′,5′,7-trimethoxyflavylium
Systematic IUPAC name
3,5-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-1λ4 -benzopyran-1-ylium
Identifiers
151776-57-7 Y (chloride): 4092-66-4 Y
ChEBI
CHEBI:5728 N
ChemSpider
390303 N
UNII
VV9H579AR2 Y (chloride): UX37SFW7Y9 Y
InChI=1S/C18H16O7/c1-22-10-6-12(19)11-8-13(20)18(25-14(11)7-10)9-4-15(23-2)17(21)16(5-9)24-3/h4-8H,1-3H3,(H2-,19,20,21)/p+1
N Key: JGPCLGHKWGCWNO-UHFFFAOYSA-O
N InChI=1/C18H16O7/c1-22-10-6-12(19)11-8-13(20)18(25-14(11)7-10)9-4-15(23-2)17(21)16(5-9)24-3/h4-8H,1-3H3,(H2-,19,20,21)/p+1
Key: JGPCLGHKWGCWNO-IKLDFBCSAS
Oc1cc2c(O)cc(OC)cc2[o+]c1c3cc(OC)c(O)c(OC)c3
Properties
C18 H17 O7 +
Molar mass
345.32 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Hirsutidin is an O-methylated anthocyanidin , a chemical compound belonging to the anthocyanins. It can be found in Catharanthus roseus [1] (Madagascar periwinkle) where it is the prominent compound in petals and can also be found in callus cultures.[2]
Glycosides
3-O-(6-O-p-coumaroyl ) glucoside of hirsutidin can also be found in Catharanthus roseus .[3]
References
^ Characterization of the anthocyanins of Catharanthus roseus (L.) G. Don in vivo and in vitro by electrospray ionization ion trap mass spectrometry, Anna Piovan, Raffaella Filippini, Donata Favretto, 1998
^ Catharanthus flavonoids on Schroeder page, uni. Freiburg, Germany
^ Piovan, Anna; Filippini, Raffaella (2007). "Anthocyanins in Catharanthus roseus in vivo and in vitro: A review". Phytochemistry Reviews . 6 (2–3): 235–242. Bibcode :2007PChRv...6..235P. doi :10.1007/s11101-006-9052-y. S2CID 676724.
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins (anthocyaninidin glycosides)Glucosides:
Diglucosides:
Cyanin (Cyanidin 3,5-O -diglucoside )
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O -diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)
Others glycosides:
Antirrhinin (Cyanidin 3-O -rutinoside)
Ideain (Cyanidin 3-O -galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O -galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O -rutinoside)Acylated anthocyanins
Acetylated anthocyanins
Cyanidin 3-O-(6-acetyl)glucoside
Delphinidin 3-O-(6-acetyl)glucoside
Malvidin 3-O-(6-acetyl)glucoside
Petunidin 3-O-(6-acetyl)galactoside
Petunidin 3-O-(6-acetyl)glucoside
Peonidin 3-O-(6-acetyl)glucoside
Coumaroylated anthocyanins (cis - and trans -) Caffeoylated anthocyanins
Malvidin 3-O-(6-p-caffeoyl)glucoside
Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins
Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides
Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
Petanin (petunidin 3-[6-O -(4-O -(E )-p -coumaroyl-O -α-l-rhamnopyranosyl)-β-D -glucopyranoside]-5-O -β-D -glucopyranoside)
Violdelphin (Delphinidin 3-rutinoside-7-O -(6-O -(4-(6-O -(4-hydroxybenzoyl)-β-D -glucosyl)oxybenzoyl)-β-D -glucoside)
Flavanol-anthocyanin adducts
Malvidin glucoside-ethyl-catechin
Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
Miscellaneous