Abietic acid

Chembox new
Name = Abietic acid [cite web
url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10569
title=ABIETIC ACID - PubChem Public Chemical Database
publisher=pubchem.ncbi.nlm.nih.gov
accessdate=2008-05-16
last=
first=]
ImageFile = Abietic acid.svg
ImageSize =
IUPACName = (1R,4aR,4bR,10aR)-7-isopropyl- 1,4a-dimethyl-1,2,3,
4,4a,4b,5,6,10,10a- decahydrophenanthrene-1- carboxylic acid
OtherNames = Abietic acid
Sylvic acid
Section1 = Chembox Identifiers
CASNo = 514-10-3
EINECS = 208-173-3
PubChem = 10569
SMILES = O=C(O)C1(C2C(C3C(=CC2) C=C(CC3)C(C)C)(CCC1)C)C
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
RTECS = TP8580000
Section2 = Chembox Properties
C=20|H=30|O=2
Appearance = yellow resinous powder, crystals or chunks
MeltingPt = 139 - 142 °C
BoilingPt = 250 °C at 9 mmHg
Solubility = Insoluble
Section7 = Chembox Hazards
NFPA-H = 1
NFPA-F = 0
NFPA-R = 0
NFPA-O =
MainHazards = Irritant
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/AB/abietic_acid.html MSDS]
RPhrases = R36/37/38
SPhrases = S26 S36

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".

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.

References

External links

* [http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7477 Abietic acid] at R&D Chemicals