Abietic acid

Structural formula
General
Surname	Abietic acid
other names	Sylvic acid; β-pimarabietic acid; Abieta-7,14-diene-19-carboxylic acid; (1 R , 4a R , 4b R , 10a R ) -1,4a-dimethyl-7-propan-2-yl-2,3,4,4b, 5,6,10,10a-octahydrophenanthrene-1-carboxylic acid ( IUPAC ) ;
Molecular formula	C 20 H 30 O 2
Brief description	colorless to yellowish monoclinic plates with a characteristic odor
External identifiers / databases
EC number	208-178-3
ECHA InfoCard	100.007.436
PubChem	10569
ChemSpider	10127
Wikidata	Q321068
properties
Molar mass	302.46 g mol −1
Physical state	firmly
Melting point	172-175 ° C
boiling point	250 ° C
solubility	practically insoluble in water ; soluble in ethanol and diethyl ether ;
safety instructions
H and P phrases	H: 315-319-335-410
	P: 302 + 352-337 + 313-304 + 340-312-280-332 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Abietic acid (from the Latin abies "fir") is a resin acid , ie a component of tree resin . Abietic acid belongs to the group of tricyclic diterpene - carboxylic acids . The esters and salts of abietic acid are called abietates.

Occurrence

Baltic amber

The optically active abietic acid is the main component of rosin . Abietic acid derivatives form the basic substance of amber .

Extraction

If pine resins are heated to over 100 ° C in closed kettles, water and turpentine oil distill over, while the melt remaining in the kettle solidifies as it cools into a vitreous mass - called rosin - the main component of which (up to 90 percent, but only around 43 percent) which is abietic acid including various isomers ( neoabietic acid , levopimaric acid and others).

properties

Pure abietic acid is colorless, usually a yellowish, glassy solidified, partially crystalline solid with a melting range of 172 to 175 ° C commercially available . Abietic acid is insoluble in water, but it dissolves well in alcohol , acetone , ether , benzene and glacial acetic acid . Abietic acid and especially its oxidation products are contact allergens .

use

Abietic acid (as molten rosin) is reacted with maleic anhydride and then esterified with polyalcohols. The resulting synthetic resin polyesters are used in printing ink resins.

Abietic acid is also used as an additive in lactic acid and butyric acid fermentation ( biotechnological production of these acids ).

Web links

Wiktionary: Abietic acid - explanations of meanings, word origins, synonyms, translations

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on abietic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d Entry on abietic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 5, 2014.
↑ Detection and quantitative determination of the resin ( Memento from August 19, 2014 in the Internet Archive ) (PDF), accessed on August 15, 2014
↑ Wiesbadener Tagblatt: Explosion transforms resin factory into a sea of flames ( Memento from February 26, 2013 in the Internet Archive ), October 14, 2000.

[GESTIS-1] Entry on abietic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[roempp-2] Entry on abietic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 5, 2014.

[3] Detection and quantitative determination of the resin ( Memento from August 19, 2014 in the Internet Archive ) (PDF), accessed on August 15, 2014

[4] Wiesbadener Tagblatt: Explosion transforms resin factory into a sea of flames ( Memento from February 26, 2013 in the Internet Archive ), October 14, 2000.