Plicatic acid

Source: Wikipedia, the free encyclopedia.
Plicatic acid
Names
IUPAC name
(7′β,8β,8′α)-3′,4,4′,8,8′,9-Hexahydroxy-5,5′-dimethoxy-2,7′-cyclolignan-9-oic acid
Systematic IUPAC name
(1S,2S,3R)-1-(3,4-Dihydroxy-5-methoxyphenyl)-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C20H22O10/c1-29-14-5-10-7-19(27,8-21)20(28,18(25)26)16(11(10)6-12(14)22)9-3-13(23)17(24)15(4-9)30-2/h3-6,16,21-24,27-28H,7-8H2,1-2H3,(H,25,26)/t16-,19+,20+/m0/s1 checkY
    Key: PGFBYAIGHPJFFJ-PWIZWCRZSA-N checkY
  • InChI=1/C20H22O10/c1-29-14-5-10-7-19(27,8-21)20(28,18(25)26)16(11(10)6-12(14)22)9-3-13(23)17(24)15(4-9)30-2/h3-6,16,21-24,27-28H,7-8H2,1-2H3,(H,25,26)/t16-,19+,20+/m0/s1
    Key: PGFBYAIGHPJFFJ-PWIZWCRZBT
  • O=C(O)[C@]2(O)[C@H](c1c(cc(OC)c(O)c1)C[C@@]2(O)CO)c3cc(O)c(O)c(OC)c3
Properties
C20H22O10
Molar mass 422.386 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Plicatic acid is a

contact allergen present in thuja wood; in contrast to pine, where the primary irritant is abietic acid
.

The highest concentrations of plicatic acid can be found in

Cryptomeria japonica
(sugi) contain it in significant proportions as well.

Exposure to plicatic acid or Thuja wood dust can worsen

References