Quillaic acid

Structural formula
General
Surname	Quillaic acid
other names	Quillaja sapogenin; 3beta, 16alpha-dihydroxy-23-oxoolean-12-en-28-one acid; (4a R , 5 R , 6a R , 6a S , 6b R , 8a R , 9 S , 10 S , 12a R , 14b S ) -9-formyl-5,10-dihydroxy-2,2,6a, 6b, 9,12a-hexamethyl-1,3,4,5,6,6a, 7,8,8a, 10,11,12,13,14b-tetradecahydropicen-4a-carbonic acid ( IUPAC );
Molecular formula	C 30 H 46 O 5
External identifiers / databases
EC number	211-149-8
ECHA InfoCard	100.010.137
PubChem	101810
ChemSpider	91986
Wikidata	Q27108137
properties
Molar mass	486.69 g mol −1
Physical state	firmly
Melting point	294 ° C
solubility	soluble in ethanol , ether , acetone , glacial acetic acid
Refractive index	56.1 ° (pyridine)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Quillajic acid (synonym Quillaja sapogenin ) is a chemical compound from the group of triterpenes .

Occurrence and use

Soap bark tree ( Quillaja saponaria )

Quillaja acid is produced by the soap bark tree ( Quillaja saponaria ). By glycosylation , inter alia, fucose and apiose arise glycosides saponins , as the extract QS-21 purified and used as an adjuvant in vaccines can be used. Accordingly, synthetic analogs of QS-21 are generated from quillajic acid. Quillajic acid used to refer to the saponins contained in QS-21, today only unglycosylated sapogenin ( aglycon of saponins).

literature

ZI Rajput, SH Hu, CW Xiao, AG Arijo: Adjuvant effects of saponins on animal immune responses. In: Journal of Zhejiang University. Science. B. Volume 8, Number 3, March 2007, pp. 153-161, doi : 10.1631 / jzus.2007.B0153 , PMID 17323426 , PMC 1810383 (free full text).

Individual evidence

↑ ^a ^b Quillaic acid data sheet from Sigma-Aldrich , accessed on February 15, 2018 ( PDF ).

↑ ^a ^b ^c RÖMPP Lexikon Chemie, 10th edition, 1996-1999. Georg Thieme Verlag, 2014, ISBN 978-3-132-00051-3 , p. 361.

↑ A. Fernández-Tejada, EK Chea, C. George, N. Pillarsetty, JR Gardner, PO Livingston, G. Ragupathi, JS Lewis, DS Tan, DY Gin: Development of a minimal saponin vaccine adjuvant based on QS-21. In: Nature chemistry. Volume 6, number 7, July 2014, pp. 635-643, doi : 10.1038 / nchem. 1963 , PMID 24950335 , PMC 4215704 (free full text).

↑ W. Karrer: Constitution and occurrence of organic plant substances (excluding alkaloids). Springer-Verlag, 2013, ISBN 978-3-034-85142-8 , p. 817.

[Sigma-1] Quillaic acid data sheet from Sigma-Aldrich , accessed on February 15, 2018 ( PDF ).

[Römpp-2] RÖMPP Lexikon Chemie, 10th edition, 1996-1999. Georg Thieme Verlag, 2014, ISBN 978-3-132-00051-3 , p. 361.

[3] A. Fernández-Tejada, EK Chea, C. George, N. Pillarsetty, JR Gardner, PO Livingston, G. Ragupathi, JS Lewis, DS Tan, DY Gin: Development of a minimal saponin vaccine adjuvant based on QS-21. In: Nature chemistry. Volume 6, number 7, July 2014, pp. 635-643, doi : 10.1038 / nchem. 1963 , PMID 24950335 , PMC 4215704 (free full text).

[Karrer-4] W. Karrer: Constitution and occurrence of organic plant substances (excluding alkaloids). Springer-Verlag, 2013, ISBN 978-3-034-85142-8 , p. 817.