Valerenic acid

Names

[ Name ]:
Valerenic acid

[Synonym ]:
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

Biological Activity

[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 Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling 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

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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...

Related Compounds

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