Dactylifric acid

Dactylifric acid
Names
	Preferred IUPAC name (3R,4R,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohex-1-ene-1-carboxylic acid
	Other names Dattelic acid; 5-O-Caffeoylshikimic acid; trans-5-O-Caffeoylshikimic acid; 5-Caffeoylshikimic acid
Identifiers
CAS Number	73263-62-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2106;
ChemSpider	4445076;
PubChem CID	5281762;
UNII	5U399BD0RZ;
	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/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1 Key: QMPHZIPNNJOWQI-GDDAOPKQSA-N;
	SMILES C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O;
Properties
Chemical formula	C16H16O8
Molar mass	336.296 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

Dactylifric acid (also known as dattelic acid or 5-O-caffeoylshikimic acid^[2]^[3]^[4]) is an ester derived from caffeic acid and shikimic acid. It and its isomers are enzymic browning substrates found in dates (Phoenix dactylifera fruits).^[3]^[5]

Some older sources identify dactylifric acid as 3-O-caffeoylshikimic acid.^[5]

Chemical structure of 3-O-caffeoylshikimic acid

References[]

^ "5-O-Caffeoylshikimic acid". CAS Common Chemistry.
^ Fukuoka, Masamichi (1982). "Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. Latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor". Chemical and Pharmaceutical Bulletin. 30 (9): 3219–3224. doi:10.1248/cpb.30.3219. PMID 6926750. 5-O-Caffeoylshikimic acid (dactylifric acid) was isolated...
^ ^a ^b Ziouti, A.; Modafar, C.; Fleuriet, A.; Boustani, S.; Macheix, J. J. (1996). "Phenolic compounds in date palm cultivars sensitive and resistant to Fusarium oxysporum". Biologia Plantarum. 38 (3): 451–457. doi:10.1007/BF02896679. S2CID 38035795. 5-caffeoylshikimic acid (dactylifric acid) and its positional isomers (3-caffeoylshikimic acid and 4-caffeoylshikimic acid)...
^ "Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity" (PDF). Trivial Name: Dactylifric acid ... Current Interpretation with IUPAC numbering: 5-O-Caffeoylshikimic acid
^ ^a ^b Maier, V. P.; Metzler, D. M.; Huber, A. F. (1964). "3-O-Caffeoylshikimic acid (dactylifric acid) and its isomers, a new class of enzymic browning substrates". Biochemical and Biophysical Research Communications. 14 (2): 124–128. doi:10.1016/0006-291x(64)90241-4. PMID 5836492.

External links[]

Dactylifric acid at the Human Metabolome Database

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[1] "5-O-Caffeoylshikimic acid". CAS Common Chemistry.

[2] Fukuoka, Masamichi (1982). "Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. Latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor". Chemical and Pharmaceutical Bulletin. 30 (9): 3219–3224. doi:10.1248/cpb.30.3219. PMID 6926750. 5-O-Caffeoylshikimic acid (dactylifric acid) was isolated...

[Ziouti-3] Ziouti, A.; Modafar, C.; Fleuriet, A.; Boustani, S.; Macheix, J. J. (1996). "Phenolic compounds in date palm cultivars sensitive and resistant to Fusarium oxysporum". Biologia Plantarum. 38 (3): 451–457. doi:10.1007/BF02896679. S2CID 38035795. 5-caffeoylshikimic acid (dactylifric acid) and its positional isomers (3-caffeoylshikimic acid and 4-caffeoylshikimic acid)...

[4] "Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity" (PDF). Trivial Name: Dactylifric acid ... Current Interpretation with IUPAC numbering: 5-O-Caffeoylshikimic acid

[Maier-5] Maier, V. P.; Metzler, D. M.; Huber, A. F. (1964). "3-O-Caffeoylshikimic acid (dactylifric acid) and its isomers, a new class of enzymic browning substrates". Biochemical and Biophysical Research Communications. 14 (2): 124–128. doi:10.1016/0006-291x(64)90241-4. PMID 5836492.

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