Plicatic acid

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Plicatic acid
Plicatic acid.svg
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
PubChem CID
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 Yes check.svgY
    Key: PGFBYAIGHPJFFJ-PWIZWCRZSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Plicatic acid is a carboxylic acid from the resin acid group. It is naturally found in Thuja and cypress resin. It is the main irritant and 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 Thuja plicata (western red cedar), but Thuja occidentalis (eastern arborvitae) and Cryptomeria japonica (sugi) contain it in significant proportions as well.

Exposure to plicatic acid or Thuja wood dust can worsen asthma and provoke allergic reactions. [1]

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Thuja occidentalis, also known as northern white-cedar, eastern white-cedar, or arborvitae, is an evergreen coniferous tree, in the cypress family Cupressaceae, which is native to eastern Canada and much of the north-central and northeastern United States. It is widely cultivated as an ornamental plant. It is not to be confused with Juniperus virginiana.

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<span class="mw-page-title-main">Hinokitiol</span> Chemical compound

Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.

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References

  1. Ayars, GH; Altman, LC; Frazier, CE; Chi, EY (1989). "The toxicity of constituents of cedar and pine woods to pulmonary epithelium". The Journal of Allergy and Clinical Immunology. 83 (3): 610–8. doi: 10.1016/0091-6749(89)90073-0 . PMID   2926083.