Plicatic acid

Plicatic acid
Names
	IUPAC name (1S,2S,3R)-1-(3,4-Dihydroxy-5-methoxyphenyl)-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid
Identifiers
CAS Number	16462-65-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	94630 ;
PubChem CID	104836;
UNII	G3VF11QD86 ;
CompTox Dashboard (EPA)	DTXSID40894748 ;
	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 Key: PGFBYAIGHPJFFJ-PWIZWCRZSA-N ; 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	422.386 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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. doi:10.1016/0091-6749(89)90073-0. PMID 2926083.

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[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.