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Dactylifric acid

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Dactylifric acid
Chemical structure of dactylifric acid
Names
Preferred IUPAC name (3R,4R,5R)-3-{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)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: QMPHZIPNNJOWQI-GDDAOPKQSA-N
SMILES
  • C1(((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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

Some older sources identify dactylifric acid as 3-O-caffeoylshikimic acid.

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. ^ 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. ^ 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

Types of hydroxycinnamic acids
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
Oligomeric forms
Dimers
Trimers
Tetramers
Conjugates with
coenzyme A (CoA)
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