(±)-2-Propyl-4-pentenoic acid (4-en-VPA) is the main toxic metabolite of Valproic acid. (±)-2-Propyl-4-pentenoic acid is neuroteratogenic.

Physicochemical Properties

Molecular Formula	C8H14O2
Molecular Weight	142.20
Exact Mass	142.099
CAS #	1575-72-0
PubChem CID	104896
Appearance	Colorless to light yellow liquid
Density	0.943g/cm3
Boiling Point	228.8ºC at 760mmHg
Flash Point	126.2ºC
Vapour Pressure	0.0257mmHg at 25°C
Index of Refraction	1.448
LogP	2.063
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Heavy Atom Count	10
Complexity	118
Defined Atom Stereocenter Count	0
SMILES	C(C(CC=C)C(O)=O)CC
InChi Key	UMYDNZXEHYSVFY-UHFFFAOYSA-N
InChi Code	InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10)
Chemical Name	2-propylpent-4-enoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	(±)-2-Propyl-4-pentenoic acid (1 mM; 26 h) causes about 50% of mouse embryos that are dysmorphogenic[2].
ADME/Pharmacokinetics	Metabolism / Metabolites 4-ene-valproate is a known human metabolite of valproic acid.
References	[1]. A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its alpha-fluorinated analogue: phase II metabolism and pharmacokinetics. Drug Metab Dispos. 1997 Feb;25(2):219-27. [2]. In vitro neuroteratogenicity of valproic acid and 4-en-VPA. Neurotoxicol Teratol. Jul-Aug 1995;17(4):425-35.
Additional Infomation	2-n-Propyl-4-pentenoic acid is a methyl-branched fatty acid.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (703.23 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (17.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (17.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (17.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	7.0323 mL	35.1617 mL	70.3235 mL
	5 mM	1.4065 mL	7.0323 mL	14.0647 mL
	10 mM	0.7032 mL	3.5162 mL	7.0323 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.