Valerenic acid
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| Category | Others |
| Catalog number | BBF-05689 |
| CAS | 3569-10-6 |
| Molecular Weight | 234.33 |
| Molecular Formula | C15H22O2 |
| Purity | ≥99% by HPLC |
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Description
Valerenic acid is a positive allosteric modulator of GABAA receptors displaying selectivity for receptors containing β2 or β3 subunits. Valerenic acid exhibits sedative, anticonvulsant and anxiolytic effects in vivo. Valerenic acid also acts as a partial agonist of 5-HT5A receptors.
Specification
| Synonyms | valerinic acid; (-)-valerenic acid |
| IUPAC Name | (E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid |
| Canonical SMILES | CC1CCC(C2=C(CCC12)C)C=C(C)C(=O)O |
| InChI | InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1 |
| InChI Key | FEBNTWHYQKGEIQ-SUKRRCERSA-N |
Properties
| Boiling Point | 481.4±38.0°C (Predicted) |
| Density | 0.996±0.06 g/cm3 (Predicted) |
Reference Reading
1.Revised structures of nardal and nardin: identity with valerenal and valerenic acid.
Kadam SH1, Paknikar SK1, Rao GV2. Nat Prod Commun. 2013 Nov;8(11):1513-4.
Structure 2 assigned presently to nardin is revised to that of valerenic acid (4), and structure 1 assigned presently to nardal is revised to that of valerenal (3). The names valerenic acid and valerenal have priority so the names nardin and nardal should no longer be used.
2.Identification of the putative binding pocket of valerenic acid on GABAA receptors using docking studies and site-directed mutagenesis.
Luger D1, Poli G2, Wieder M3, Stadler M1, Ke S1, Ernst M4, Hohaus A1, Linder T1, Seidel T3, Langer T3, Khom S1, Hering S1. Br J Pharmacol. 2015 Nov;172(22):5403-13. doi: 10.1111/bph.13329. Epub 2015 Oct 25.
BACKGROUND AND PURPOSE: β2/3-subunit-selective modulation of GABAA receptors by valerenic acid (VA) is determined by the presence of transmembrane residue β2/3N265. Currently, it is not known whether β2/3N265 is part of VA's binding pocket or is involved in the transduction pathway of VA's action. The aim of this study was to clarify the localization of VA's binding pocket on GABAA receptors.
3.The anxiolytic effects of a Valerian extract is based on valerenic acid.
Becker A, Felgentreff F, Schröder H, Meier B, Brattström A1. BMC Complement Altern Med. 2014 Jul 28;14:267. doi: 10.1186/1472-6882-14-267.
BACKGROUND: Valerian is commonly used for the treatment of insomnia and anxiety. Valerian extracts allosterically modulate GABA-A receptors and induced an anxiolytic activity. This activity is closely related to valerenic acid. In the present experiments it was investigated whether acetoxy valerenic acid may interfere with the anxiolytic action of valerenic acid.
4.Impact of Altitudes and Habitats on Valerenic Acid, Total Phenolics, Flavonoids, Tannins, and Antioxidant Activity of Valeriana jatamansi.
Jugran AK1, Bahukhandi A1, Dhyani P1, Bhatt ID2, Rawal RS1, Nandi SK1. Appl Biochem Biotechnol. 2016 Mar 14. [Epub ahead of print]
The changes in total phenolics, flavonoids, tannins, valerenic acid, and antioxidant activity were assessed in 25 populations of Valeriana jatamansi sampled from 1200 to 2775 m asl and four habitat types of Uttarakhand, West Himalaya. Significant (p < 0.05) variations in total phenolics, flavonoids, valerenic acid, and antioxidant activity in aerial and root portions and across the populations were observed. Antioxidant activity measured by three in vitro antioxidant assays, i.e., 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic) (ABTS) radical scavenging, 2,2'-diphenyl-1-picryylhydrazyl (DPPH) free radical scavenging, and ferric-reducing antioxidant power (FRAP) assays, showed significant (p < 0.05) differences across the populations. However, no clear pattern was found in phytochemicals across the altitudinal range. Among habitat types, (pine, oak, mixed forest, and grassy land), variation in phytochemical content and antioxidant activity were observed.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
