CAS 3569-10-6|Valerenic acid
| Common Name | Valerenic acid | ||
|---|---|---|---|
| CAS Number | 3569-10-6 | Molecular Weight | 234.334 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 374.5±21.0 °C at 760 mmHg |
| Molecular Formula | C15H22O2 | Melting Point | 134-139ºC |
| MSDS | ChineseUSA | Flash Point | 274.2±13.0 °C |
Names
| Name | valerenic acid |
|---|---|
| Synonym | More Synonyms |
Valerenic acid BiologicalActivity
| Description | Valerenic acid ((-)-Valerenic Acid), a sesquiterpenoid, is an orally active positive allosteric modulator of GABAA receptors. Valerenic acid is also a partial agonist of the 5-HT5a receptor. Valerenic acid mediates anxiolytic activity via GABAA receptors containing the β3 subunit. Valerenic acid also exhibits potent antioxidant properties[1][2][3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorResearch Areas >>Neurological DiseaseSignaling Pathways >>Neuronal Signaling >>GABA ReceptorSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT Receptor |
| Target | 5-HT5A Receptor:17.2 μM (IC50) GABAA |
| In Vitro | Valerenic acid (1-100 μM) enhances the whole cell currents on GABAA receptors expressed in HEK 293 cells[1]. Valerenic acid exhibits significant affinity for the 5-HT5a receptor, with an IC50 of 17.2 μM (Ki=10.7 μM)[2]. [3H]Valerenic acid binds to brain membranes reveals both a high affinity binding site (KD=25 nM) and a low affinity site (KD=16 μM)[1]. [3H]Valerenic acid is displaced by Valerenol with high potency (IC50=3 nM)[1]. |
| In Vivo | Valerenic acid (1-6 mg/kg i.p. or 10 mg/kg p.o.) decreases the aversion of wild type mice to the lit area[2]. Valerenic acid (10 mg/kg; p.o.) increases the proportion of time 129X1/SvJ mice spent onto the open arms[2]. |
| References | [1]. Benke D, et, al. GABA A receptors as in vivo substrate for the anxiolytic action of valerenic acid, a major constituent of valerian root extracts. Neuropharmacology. 2009 Jan;56(1):174-81. [2]. Dietz BM, et, al. Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. Brain Res Mol Brain Res. 2005 Aug 18;138(2):191-7. [3]. Kara M, et, al. Ameliorative Effects of the Sesquiterpenoid Valerenic Acid on Oxidative Stress Induced in HepG2 Cells after Exposure to the Fungicide Benomyl. Antioxidants (Basel). 2021 May 8;10(5):746. [4]. Becker A, et, al. The anxiolytic effects of a Valerian extract is based on valerenic acid. BMC Complement Altern Med. 2014 Jul 28;14:267. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 374.5±21.0 °C at 760 mmHg |
| Melting Point | 134-139ºC |
| Molecular Formula | C15H22O2 |
| Molecular Weight | 234.334 |
| Flash Point | 274.2±13.0 °C |
| Exact Mass | 234.161987 |
| PSA | 37.30000 |
| LogP | 5.13 |
| Vapour Pressure | 0.0±1.8 mmHg at 25°C |
| Index of Refraction | 1.529 |
| InChIKey | FEBNTWHYQKGEIQ-SUKRRCERSA-N |
| SMILES | CC(=CC1CCC(C)C2CCC(C)=C12)C(=O)O |
| Storage condition | −20°C |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
Articles28
More Articles| Concise synthesis of Valerena-4,7(11)-diene, a highly active sedative, from valerenic acid. Biosci. Biotechnol. Biochem. 74(9) , 1963-4, (2010) A concise synthesis of valerena-4,7(11)-diene with potent sedative activity was achieved in three steps involving, reduction of carboxylic acid, bromination of the resulting alcohol, and reduction of ... | |
| Root colonization by symbiotic arbuscular mycorrhizal fungi increases sesquiterpenic acid concentrations in Valeriana officinalis L. Planta Med. 76(4) , 393-8, (2010) In some medicinal plants a specific plant-fungus association, known as arbuscular mycorrhizal (AM) symbiosis, increases the levels of secondary plant metabolites and/or plant growth. In this study, th... | |
| Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. Brain Res. Mol. Brain Res. 138(2) , 191-7, (2005) Insomnia is the most frequently encountered sleep complaint worldwide. While many prescription drugs are used to treat insomnia, extracts of valerian (Valeriana officinalis L., Valerianaceae) are also... |
Synonyms
| 2-Propenoic acid, 3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)- |
| MFCD00075694 |
| (2E)-3-[(4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid |
| 7-Hydroxy-PIPAT maleate |
| (2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid |
| Valerenic acid |
| Valerenic acid,(2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexadydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoicacid |
