Abietic acid

Abietic acid

Names
IUPAC name Abieta-7,13-dien-18-oic acid
Other names (1R,4aR,4bR,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid; Abietinic acid; Sylvic acid
Identifiers
CAS Number	514-10-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28987 Y
ChEMBL	ChEMBL71893 Y
ChemSpider	10127 Y
ECHA InfoCard	100.007.436
EC Number	208-173-3
KEGG	C06087 Y
PubChem	10569
RTECS number	TP8580000
UNII	V3DHX33184 Y
InChI InChI=1S/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 Y Key: RSWGJHLUYNHPMX-ONCXSQPRSA-N Y 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 Key: RSWGJHLUYNHPMX-ONCXSQPRBK
SMILES O=C(O)[C@]3([C@@H]2C/C=C1/C=C(\CC[C@@H]1[C@@]2(C)CCC3)C(C)C)C
Properties
Chemical formula	C20H30O2
Molar mass	302.46 g·mol−1
Appearance	Yellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water). Colorless solid when pure.
Density	1.06 g/mL
Melting point	172–175 °C (342–347 °F; 445–448 K)
Solubility in water	Insoluble
Solubility in other solvents	Very soluble in acetone, petroleum ether, Et2O, and ethanol
Hazards
Main hazards	Irritant
Safety data sheet	MSDS
R-phrases	R36/37/38
S-phrases	S26 S36
NFPA 704	0 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Abietic acid (also known as abietinic acid or sylvic acid) is an organic compound that occurs widely in trees. It is the primary component of 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 or salt is called an abietate.

Abietic acid is extracted from tree rosin. The pure material is a colorless solid, but commercial samples are usually a glassy or partly crystalline yellowish solid that melts at temperatures as low as 85 °C (185 °F).

It belongs to the abietane diterpene group of organic 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 found in Pinus insularis (Khasi Pine), Pinus kesiya Royle, Pinus strobus (Eastern White Pine), and Pinus sylvestris (Scots Pine).

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 otherwise soft, tacky, and low-melting and subject to rapid deterioration by oxidation in air. Stability is greatly increased by heat treatment.