Valerenic acid

Structural formula
General
Surname	Valerenic acid
other names	(2 E ) -3 - [(4 S , 7 R , 7a R ) -3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1 H -inden-4-yl] -2 -methacrylic acid ( IUPAC )
Molecular formula	C 15 H 22 O 2
Brief description	colorless and odorless solid
External identifiers / databases
EC number	609-163-8
ECHA InfoCard	100.112.154
PubChem	6440940
ChemSpider	4788689
Wikidata	Q75850
properties
Molar mass	234.34 g mol −1
Physical state	firmly
Melting point	140-142 ° C
solubility	poorly soluble in water; easily soluble in ethanol;
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 .

Valerenic acid is a bicyclic sesqui terpene that occurs in real valerian ( Valeriana officinalis ). There it serves as an indicator, since it is not contained in most other species of the genus Valeriana . Valerenic acid is not to be confused with valeric acid , which is a common name for pentanoic acid, which is also found in real valerian.

Valerenic acid has a muscle-relaxing , spasmolytic and CNS-depressing effect .

Valerenic acid is an allosteric modulator of the GABA _A receptor and has the effect of increasing the current of chloride (chloride stimulation). This effect is limited solely to channels that contain β ₂ or β ₃ subunits. The acid docked probably the loreclezole - binding site and is as anxiolytic significantly more effective than its ethyl ester . The receptor-modulating activity is exceeded by the isosteric tetrazole compound, in which the carboxyl group is replaced by an equally acidic tetrazole ring.

In addition, valerenic acid and related sesquiterpenes inhibit the breakdown of the neurotransmitter γ-aminobutyric acid (GABA).

Valerenic acid acts as a partial agonist at the 5-HT _5A receptor .

Web links

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

Individual evidence

↑ ^a ^b ^c Ernst Steinegger, Rudolf Hansel: Textbook of Pharmacognosie and Phytopharmacy . Springer-Verlag, 2013, ISBN 978-3-662-08318-5 , pp. 171 ( limited preview in Google Book search).
↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM Additives, Flavors, and Ingredients . CRC Press, 2003, ISBN 978-1-4200-6845-0 , pp. 1422 ( limited preview in Google Book search).
↑ ^a ^b Data sheet Valerenic acid, analytical standard from Sigma-Aldrich , accessed on June 19, 2019 ( PDF ).
↑ ^a ^b S. Khom, I. Baburin, S. Hering u. a .: Valerenic Acid Potentiates and Inhibits GABAA Receptors: Molecular Mechanism and Subunit Specificity. In: Neuropharmacology . 53 (1), 2007, pp. 178-187, PMID 17585957 .
^ F. Felgentreff, A. Becker, B. Meier, A. Brattström: Valerian extract characterized by high valerenic acid and low acetoxy valerenic acid contents demonstrates anxiolytic activity . In: Phytomedicine . tape 19 , no. 13 , 2012, p. 1216-1222 , doi : 10.1016 / j.phymed.2012.08.003 , PMID 22944521 .
↑ S. Kopp, R. Baur, E. Sigel, H. Möhler, KH Altmann: Highly potent modulation of GABA (A) receptors by valerenic acid derivatives . In: ChemMedChem . tape 5 , no. 5 , 2010, p. 678-681 , doi : 10.1002 / cmdc.201000062 , PMID 20235267 .
↑ BM Dietz u. a .: Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. In: Brain Res. Mol. Brain Res. 138 (2), 2005, pp. 191-197, PMID 15921820 .

[Ernst_Steinegger,_Rudolf_Hänsel-1] Ernst Steinegger, Rudolf Hansel: Textbook of Pharmacognosie and Phytopharmacy . Springer-Verlag, 2013, ISBN 978-3-662-08318-5 , pp. 171 ( limited preview in Google Book search).

[Shmuel_Yannai-2] Shmuel Yannai: Dictionary of Food Compounds with CD-ROM Additives, Flavors, and Ingredients . CRC Press, 2003, ISBN 978-1-4200-6845-0 , pp. 1422 ( limited preview in Google Book search).

[Sigma-3] Data sheet Valerenic acid, analytical standard from Sigma-Aldrich , accessed on June 19, 2019 ( PDF ).

[Khom-4] S. Khom, I. Baburin, S. Hering u. a .: Valerenic Acid Potentiates and Inhibits GABAA Receptors: Molecular Mechanism and Subunit Specificity. In: Neuropharmacology . 53 (1), 2007, pp. 178-187, PMID 17585957 .

[5] F. Felgentreff, A. Becker, B. Meier, A. Brattström: Valerian extract characterized by high valerenic acid and low acetoxy valerenic acid contents demonstrates anxiolytic activity . In: Phytomedicine . tape 19 , no. 13 , 2012, p. 1216-1222 , doi : 10.1016 / j.phymed.2012.08.003 , PMID 22944521 .

[6] S. Kopp, R. Baur, E. Sigel, H. Möhler, KH Altmann: Highly potent modulation of GABA (A) receptors by valerenic acid derivatives . In: ChemMedChem . tape 5 , no. 5 , 2010, p. 678-681 , doi : 10.1002 / cmdc.201000062 , PMID 20235267 .

[7] BM Dietz u. a .: Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. In: Brain Res. Mol. Brain Res. 138 (2), 2005, pp. 191-197, PMID 15921820 .