Valerenic acid

Base Information

• Chemical Name: Valerenic acid
• CAS No.: 3569-10-6
• Molecular Formula: C15H22 O2
• Molecular Weight: 234.338
• Hs Code.: 2916205000
• European Community (EC) Number: 609-163-8
• UNII: 34NDB285PM
• DSSTox Substance ID: DTXSID8034089
• Nikkaji Number: J14.796F
• Wikipedia: Valerenic_acid
• Wikidata: Q75850
• Metabolomics Workbench ID: 53506
• ChEMBL ID: CHEMBL1545045
• Mol file: 3569-10-6.mol

Synonyms:valerenic acid

Chemical Property of Valerenic acid

Chemical Property:

• Appearance/Colour: brown-yellow powder
• Vapor Pressure: 1.22E-06mmHg at 25°C
• Melting Point: 134-139°C
• Refractive Index: 1.528
• Boiling Point: 374.5 °C at 760 mmHg
• PKA: 4.88±0.19(Predicted)
• Flash Point: 274.2 °C
• PSA: 37.30000
• Density: 1.06 g/cm³
• LogP: 3.78990
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly),Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 390

Purity/Quality:

98%,99%, ^*data from raw suppliers

Valerenic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(C2=C(CCC12)C)C=C(C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@H](C2=C(CC[C@H]12)C)/C=C(\C)/C(=O)O
• Uses: Valerenic Acid, acts as a subtype-selective GABAA receptor agonist in neonatal rat brainstem preparations. It can be used for the synthesis of Valerena-4,7(11)-diene, a highly active sedative.

Technology Process of Valerenic acid

There total 18 articles about Valerenic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

valerenic acid ethyl ester (1123095-70-4) → valerenic acid (3569-10-6)

Guidance literature:

valerenic acid ethyl ester; With lithium hydroxide; water; In tetrahydrofuran; methanol; at 22 ℃; for 24h; Inert atmosphere;

With water; citric acid; In tetrahydrofuran; methanol; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol9000137

Reference yield:

Valerenal (4176-16-3) → valerenic acid (3569-10-6)

Guidance literature:

Valerenal; With sodium t-butanolate;

With sodium chlorite; 2-methyl-but-2-ene; disodium hydrogen phosphate monohydrate; In tert-butyl alcohol; at 20 ℃; for 5h;

DOI:10.1055/s-0029-1217378

Reference yield:

cyclopent-2-enone (930-30-3) → valerenic acid (3569-10-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: tert.-butyl lithium / diethyl ether / 2.25 h / -78 - 20 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: dipyridinium dichromate / dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: magnesium bromide diethyl etherate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.2: 6 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere

6.1: benzene / 24 h / Inert atmosphere; Reflux

7.1: Crabtree's catalyst; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere

9.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

10.2: 15.75 h / 0 - 20 °C / Inert atmosphere

11.1: water; lithium hydroxide / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

With pyridine; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; magnesium bromide diethyl etherate; Crabtree's catalyst; water; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 4.1: hydroxy-directed Diels-Alder reaction / 6.1: Wittig olefination / 10.1: Negishi coupling reaction / 10.2: Negishi coupling reaction;

DOI:10.1002/ejoc.201101834

upstream raw materials:

valerenic acid ethyl ester

Valerenal

(E)-3-((3S,3aS,4S,7R,7aR)-3-hydroxy-7-methyl-octahydro-inden-4-yl)-2-methylacrylic acid ethyl ester

(E)-2-methyl-3-((3aS,4S,7R,7aR)-7-methyl-3-oxo-octahydro-inden-4-yl)-acrylic acid ethyl ester

Downstream raw materials:

Valerenol

Refernces

• 1、 -. "METHODS FOR MAKING VALERENIC ACID DERIVATIVES AND THEIR USE". Page/Page column 114-115. . Retrieved 2010/08/08.
• 2、 Kopp, Sascha,Schweizer, W. Bernd,Altmann, Karl-Heinz. "Total synthesis of valerenic acid". scheme or table. p. 1769 - 1772. Retrieved 2009/12/04.