Talk:Dactylifric acid

Please check the stereochemistry and double bonds of the shikimic acid moeity in dactylifric acid and in shikimic acid. Seems to me, the double bond should be switched to the other side of the cycle. — Preceding unsigned comment added by 137.248.163.46 (talk • contribs) 13:29, 24 October 2014 (UTC)

Is seems to be somewhat more complicated. You're right that the structure is wrong. File:3-O-caffeoylshikimic acid.svg image currently shows 3-O-caffeoyl-4-epishikimic instead of 3-O-caffeoylshikimic acid. (I've just claimed a dispute for it). However, the assigned structure seems to be based on journal article reference, which uses “3-O-caffeoylshikimic acid” name for yet another, 5-O-caffeoylshikimic acid structure. —Mykhal (talk) 17:11, 2 July 2020 (UTC)

3-O-caffeoylshikimic acid or 5-O-caffeoylshikimic acid?

There seems to be some confusion about the chemical structure of dactylifric acid. The two sources currently in the article, Maier et al. and Human Metabolome Database indicate that dactylifric acid is 3-O-caffeoylshikimic acid (though another record at Human Metabolome Database is inconsistent). Chemical Abstracts, which I would consider the most authoritative source regarding chemical structures, indicates that dactylifric acid is 5-O-caffeoylshikimic acid - see here - and has the CAS# 73263-62-4. 3-O-caffeoylshikimic acid is listed as a different compound and has the CAS# 180981-12-8. Most modern sources equate dactylifric acid with 5-O-caffeoylshikimic acid. Here are a few examples:

• doi:10.1248/cpb.30.3219 "5-O-Caffeoylshikimic acid (dactylifric acid) was isolated..."
• doi:10.1007/BF02896679 "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 "Trivial Name: Dactylifric acid", "Current Interpretation with IUPAC numbering: 5-O-Caffeoylshikimic acid"

As far as I can tell, modern primary sources agree that dactylifric acid is 5-O-caffeoylshikimic acid. The only primary source I can find that equates dactylifric acid with 3-O-caffeoylshikimic acid is Maier et al. which is from 1964. Therefore, considering modern analytical techniques are far superior to what was available in 1964, I think the Wikipedia article should be updated to be consistent with the modern use in which dactylifric acid is equivalent to 5-O-caffeoylshikimic acid. Innerstream (talk) 23:09, 21 May 2021 (UTC)

@DMacks: Since you commented on this issue at Commons, your input here would be welcome as well. Innerstream (talk) 23:14, 21 May 2021 (UTC)