valerenic acid
2-propenoic acid, 3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)-
Identification
| Name | valerenic acid |
| IUPAC | (E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid |
| CAS Number | 3569-10-6 |
| FDA UNII | 34NDB285PM |
| Molecular Formula | C15 H22 O2 |
| Molecular Weight | 234.33874000 |
| MDL Number | MFCD00075694 |
| Nikkaji Number | J14.796F |
| Beilstein | 3138020 |
Regulatory
Physical Properties
| Appearance | yellow to brown powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 374.00 to 375.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000001 mmHg @ 25.00 °C. (est) |
| Flash Point | 525.00 °F. TCC ( 273.89 °C. ) |
| logP (o/w) | 5.188 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for valerenic acid usage levels up to | not for fragrance use. |
| Recommendation for valerenic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(2E)-3-[(4S,7R,7aR)-3,7-
dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid
(2E)-3-[(4S,7R,7aR)-3,7-
dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
(E)-3-[(4S,7R,7aR)-3,7-
dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
(2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-
hexadydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoic acid
(4S-(4alpha(E),7beta,7aalpha))-3-(2,4,5,6,7,7a-
hexahydro-3,7-dimethyl-1H-inden-4-yl)-2-methyl-2-propenoic acid
2-
propenoic acid, 3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)-
valerenicacid
valerinic acid
PubMed:
Esters of valerenic acid as potential prodrugs.
PubMed:
Revised structures of nardal and nardin: identity with valerenal and valerenic acid.
PubMed:
Valeriana officinalis extract and its main component, valerenic acid, ameliorate D-galactose-induced reductions in memory, cell proliferation, and neuroblast differentiation by reducing corticosterone levels and lipid peroxidation.
PubMed:
Antioxidant effect and study of bioactive components of Valeriana sisymbriifolia and Nardostachys jatamansii in comparison to Valeriana officinalis.
PubMed:
Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis.
PubMed:
Valerian extract characterized by high valerenic acid and low acetoxy valerenic acid contents demonstrates anxiolytic activity.
PubMed:
Anxiolytic properties of Valeriana officinalis in the zebrafish: a possible role for metabotropic glutamate receptors.
PubMed:
Enzymatic synthesis of valerena-4,7(11)-diene by a unique sesquiterpene synthase from the valerian plant (Valeriana officinalis).
PubMed:
Pharmacokinetics of valerenic acid in rats after intravenous and oral administrations.
PubMed:
Efficient and scalable one-pot synthesis of 2,4-dienols from cycloalkenones: optimized total synthesis of valerenic acid.
PubMed:
Three phases hollow fiber LPME combined with HPLC-UV for extraction, preconcentration and determination of valerenic acid in Valeriana officinalis.
PubMed:
Selective Interactions of Valeriana officinalis Extracts and Valerenic Acid with [H]Glutamate Binding to Rat Synaptic Membranes.
PubMed:
Telemetry as a tool to measure sedative effects of a valerian root extract and its single constituents in mice.
PubMed:
Pharmacokinetics of valerenic acid after single and multiple doses of valerian in older women.
PubMed:
Concise synthesis of Valerena-4,7(11)-diene, a highly active sedative, from valerenic acid.
PubMed:
Valerenic acid derivatives as novel subunit-selective GABAA receptor ligands - in vitro and in vivo characterization.
PubMed:
Highly potent modulation of GABA(A) receptors by valerenic acid derivatives.
PubMed:
Valeriana officinalis root extracts have potent anxiolytic effects in laboratory rats.
PubMed:
Root colonization by symbiotic arbuscular mycorrhizal fungi increases sesquiterpenic acid concentrations in Valeriana officinalis L.
PubMed:
Relaxing effects of Valeriana officinalis extracts on isolated human non-pregnant uterine muscle.
PubMed:
Total synthesis of valerenic acid, a potent GABAA receptor modulator.
PubMed:
Hepatic metabolism and biliary excretion of valerenic acid in isolated perfused rat livers: role of Mrp2 (Abcc2).
PubMed:
Transport of a GABAA receptor modulator and its derivatives from Valeriana officinalis L. s. l. across an in vitro cell culture model of the blood-brain barrier.
PubMed:
GABA A receptors as in vivo substrate for the anxiolytic action of valerenic acid, a major constituent of valerian root extracts.
PubMed:
HPLC-based activity profiling approach for the discovery of GABAA receptor ligands using an automated two microelectrode voltage clamp assay on Xenopus oocytes.
PubMed:
[Studies on chemical constituents of Valeriana officinalis].
PubMed:
Essential oil composition of Valeriana officinalis L. roots cultivated in Iran. Comparative analysis between supercritical CO2 extraction and hydrodistillation.
PubMed:
Modulation of GABAA receptors by valerian extracts is related to the content of valerenic acid.
PubMed:
[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].
PubMed:
Valerenic acid potentiates and inhibits GABA(A) receptors: molecular mechanism and subunit specificity.
PubMed:
Effect of valerian, valerian/hops extracts, and valerenic acid on glucuronidation in vitro.
PubMed:
NF-kappaB modulators from Valeriana officinalis.
PubMed:
Commercial valerian interactions with [3H]Flunitrazepam and [3H]MK-801 binding to rat synaptic membranes.
PubMed:
Chemical fingerprinting of valeriana species: simultaneous determination of valerenic acids, flavonoids, and phenylpropanoids using liquid chromatography with ultraviolet detection.
PubMed:
Pharmacokinetics of valerenic acid after administration of valerian in healthy subjects.
PubMed:
Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro.
PubMed:
Extraction of valerenic acids from valerian (Valeriana officinalis L.) rhizomes.
PubMed:
In vitro activity of commercial valerian root extracts against human cytochrome P450 3A4.
PubMed:
Multiple night-time doses of valerian (Valeriana officinalis) had minimal effects on CYP3A4 activity and no effect on CYP2D6 activity in healthy volunteers.
PubMed:
Stability control of valerian ground material and extracts: a new HPLC-method for the routine quantification of valerenic acids and lignans.
PubMed:
Essential oil of Valeriana officinalis L. cultivars and their antimicrobial activity as influenced by harvesting time under commercial organic cultivation.
PubMed:
Sedative and sleep-enhancing properties of linarin, a flavonoid-isolated from Valeriana officinalis.
PubMed:
The gamma-aminobutyric acidergic effects of valerian and valerenic acid on rat brainstem neuronal activity.
PubMed:
In vitro release of valerenic and hydroxyvalerenic acids from valerian tablets.
PubMed:
(-)-3 beta,4 beta-epoxyvalerenic acid from Valeriana officinalis.
PubMed:
Valepotriates and valerenic acids in commercial preparations of valerian available in Australia.
PubMed:
Analysis of sesquiterpenes in Valeriana officinalis by capillary electrophoresis.
PubMed:
Polysomnographic evaluation of the hypnotic effect of Valeriana edulis standardized extract in patients suffering from insomnia.
PubMed:
Valerenic acid derivatives and valepotriates among individuals, varieties and species of Valeriana.
PubMed:
The scientific basis for the reputed activity of Valerian.
PubMed:
Cytotoxic potential of valerian constituents and valerian tinctures.
PubMed:
Seasonal variation of the essential oil, valerenic acid and derivatives, and velopotriates in Valeriana officinalis roots and rhizomes, and the selection of plants suitable for phytomedicines.
PubMed:
In vitro study on the interaction of Valeriana officinalis L. extracts and their amino acids on GABAA receptor in rat brain.
PubMed:
Central nervous depressant activity of valerenic Acid in the mouse.
PubMed:
Central nervous depressant activity of valerenic acid in the mouse.
PubMed:
[Inhibition of gamma-aminobutyric acid catabolism by valerenic acid derivatives].