Plicatic acid

Plicatic acid
Names

IUPAC name (1S,2S,3R)-1-(3,4-Dihydroxy-5-methoxyphenyl)-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-1,4-dihydronaphthalene-2-carboxylic acid
Identifiers
CAS Number	16462-65-0^Y
3D model (JSmol)	Interactive image
ChemSpider	94630^Y
PubChem CID	104836
InChI 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^Y Key: PGFBYAIGHPJFFJ-PWIZWCRZSA-N^Y 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
SMILES 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
Chemical formula	C₂₀H₂₂O₁₀
Molar mass	422.39 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

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. (Cf. 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]

References

↑ 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. PMID 2926083. doi:10.1016/0091-6749(89)90073-0.

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