Dactylifric acid

Dactylifric acid
Names

IUPAC name 5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
Other names 3-O-Caffeoylshikimic acid
Identifiers
CAS Number	6082-44-6
3D model (Jmol)	Interactive image
ChemSpider	29420736
InChI InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-5,7,12-13,15,17-19,21H,6H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1 Key: MRDAXWGGWWDUKL-GDDAOPKQSA-N InChI=1/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-5,7,12-13,15,17-19,21H,6H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1 Key: MRDAXWGGWWDUKL-GDDAOPKQBO
SMILES C1[C@H]([C@H]([C@@H](C=C1C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
Properties
Chemical formula	C₁₆H₁₆O₈
Molar mass	336.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dactylifric acid is a caffeic acid glycoside (3-O-caffeoylshikimic acid). It and its isomers are enzymic browning substrates found in dates (Phoenix dactylifera fruits).^[1]

References

↑ Maier, VP; Metzler, DM; Huber, AF (1964). "3-O-Caffeoylshikimic acid (dactylifric acid) and its isomers, a new class of enzymic browning substrates". Biochemical and Biophysical Research Communications. 14: 124–8. doi:10.1016/0006-291x(64)90241-4. PMID 5836492.

Aglycones

Precursor	Cinnamic acid

Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid

Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid

others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid

esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Tartaric acid esters

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid

Trimers	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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