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02010595

Valerenic acid

primary reference standard

Synonym(s):

(2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexadydro-3,7-dimethyl- 1H-inden-4-yl]-2-methyl-2-propenoic acid

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About This Item

Empirical Formula (Hill Notation):
C15H22O2
CAS Number:
3569-10-6
Molecular Weight:
234.33
Beilstein:
3138020
MDL number:
MFCD00075694
UNSPSC Code:
85151701
PubChem Substance ID:
329747383
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

SMILES string

[H][C@]12CCC(C)=C1[C@@H](CC[C@H]2C)\C=C(/C)C(O)=O

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

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General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference standard in the analysis of herbal medicinal products.

Other Notes

This compound is commonly found in plants of the genus: valeriana

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
HWI03424
HWI02798-1
HWI02798
HWI00962
HWI01875-1

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Winfried Neuhaus et al.
Planta medica, 74(11), 1338-1344 (2008-08-16)
The roots and rhizome of Valeriana officinalis L . s. l. are therapeutically used for their sedative and sleep-enhancing effects. Some of the active compounds found in commonly used extracts are the sesquiterpenic acids, especially valerenic acid, which was recently
S Khom et al.
Neuropharmacology, 53(1), 178-187 (2007-06-26)
Valerian is a commonly used herbal medicinal product for the treatment of anxiety and insomnia. Here we report the stimulation of chloride currents through GABA(A) receptors (I(GABA)) by valerenic acid (VA), a constituent of Valerian. To analyse the molecular basis
Gabriele Trauner et al.
Planta medica, 74(1), 19-24 (2007-12-21)
Valeriana Officinalis L . is a traditionally used sleep remedy, however, the mechanism of action and the substances responsible for its sedative and sleep-enhancing properties are not fully understood. As we previously identified valerenic acid as a subunit-specific allosteric modulator
Highly potent modulation of GABA(A) receptors by valerenic acid derivatives.
Sascha Kopp et al.
ChemMedChem, 5(5), 678-681 (2010-03-18)
Takashi Kitayama et al.
Bioscience, biotechnology, and biochemistry, 74(9), 1963-1964 (2010-09-14)
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 the bromide from valerenic acid in a 63% total yield. This synthetic method
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