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Abietic acid



Abietic acid
IUPAC name (1R,4aR,4bR,10aR)-7-isopropyl- 1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a- decahydrophenanthrene-1-carboxylic acid
Other names Abietic acid, Sylvic acid
Identifiers
CAS number 514-10-3
PubChem 10569
EINECS number 208-173-3
RTECS number TP8580000
SMILES O=C(O)C1(C2C(C3C(=CC2)C=C(CC3)C(C)C)(CCC1)C)C
InChI InChI=1/C20H30O2/c1-13(2)14-6-8-16-15(12-14) 7-9-17-19(16,3)10-5-11-20(17,4)18(21) 22/h7,12-13,16-17H,5-6,8-11H2,1-4H3, (H,21,22)/t16-,17+,19+,20+/m0/s1
Properties
Molecular formula C20H30O2
Molar mass 302.44 g/mol
Appearance yellow resinous powder, crystals or chunks
Melting point

139 - 142 °C

Boiling point

250 °C at 9 mmHg

Solubility in water Insoluble
Hazards
MSDS MSDS
Main hazards Irritant
R-phrases R36/37/38
S-phrases S26 S36
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Abietic acid (also known as abietinic acid or sylvic acid), a resin acid, is the primary irritant in pine wood and resin, isolated from rosin (via isomerization) and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. Its ester is called an abietate.

Additional recommended knowledge

Abietic acid is a weak contact allergen, however compounds resulting of its oxidation by air elicit stronger response. It is soluble in alcohols, acetone, and ethers.

Commercial abietic acid is usually a glassy or partly crystalline, yellowish solid that melts at temperatures as low as 85° C (185° F). It belongs to the diterpene group of organic compounds (compounds derived from four isoprene units). It is used in lacquers, varnishes, and soaps, and for the analysis of resins and the preparation of metal resinates. It is listed in the Toxic Substances Control Act inventory.

Rosin has been used for centuries for caulking ships. It is also rubbed on the bows of musical instruments to make them less slippery. In modern times methods have been developed for improving the properties of the rosin acids, which are soft, tacky, and low-melting and subject to rapid deterioration by oxidation in air. Stability is greatly increased by heat treatment.

Rosin acids are converted into ester gum by reaction with controlled amounts of glycerol or other polyhydric alcohols. Ester gum has drying properties and is used in paints, varnishes, and lacquers.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Abietic_acid". A list of authors is available in Wikipedia.
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