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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
ChEBI
ChemSpider
UNII
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
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
C 16 H 16 O 8
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).
Chemical compound
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
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids)
Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
Glycosides
Tartaric acid esters Other esters with caffeic acid Caffeoyl phenylethanoid glycoside (CPG)
Echinacoside
Calceolarioside A ,
B ,
C ,
F
Chiritoside A ,
B ,
C
Cistanoside A ,
B ,
C ,
D ,
E ,
F ,
G ,
H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (
Isoverbascoside ,
2′-Acetylverbascoside )
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 Tetramers
Conjugates with
coenzyme A (CoA)