Dactylifric acid

Dactylifric acid
Chemical structure of 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
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:2106
ChemSpider
  • 4445076
PubChem CID
  • 5281762
UNII
  • 5U399BD0RZ
CompTox Dashboard (EPA)
  • DTXSID501312675 Edit this at Wikidata
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
  • 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
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

  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...
  3. ^ 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)...
  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
  5. ^ 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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Types of hydroxycinnamic acids
Aglycones
Precursor
  • Cinnamic acid
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
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
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
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
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)
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