Flavor & Fragrance
Product Name:
4-METHYL PENTANOIC ACID FCC, 4-Methylpentanoic acid, 4-Methylvaleric acid, Pentanoic acid, 4-methyl-
CAS Number:
Molecular Weight:
Molecular Formula:
Olfactive Family:
Odor description:
A pungent, cheese-like odor.
Chemical Structure

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Reference Reading

1.Efficient synthesis of D-branched-chain amino acids and their labeled compounds with stable isotopes using D-amino acid dehydrogenase.
Akita H1, Suzuki H, Doi K, Ohshima T. Appl Microbiol Biotechnol. 2014 Feb;98(3):1135-43. doi: 10.1007/s00253-013-4902-1. Epub 2013 May 10.
D-Branched-chain amino acids (D-BCAAs) such as D-leucine, D-isoleucine, and D-valine are known to be peptide antibiotic intermediates and to exhibit a variety of bioactivities. Consequently, much effort is going into achieving simple stereospecific synthesis of D-BCAAs, especially analogs labeled with stable isotopes. Up to now, however, no effective method has been reported. Here, we report the establishment of an efficient system for enantioselective synthesis of D-BCAAs and production of D-BCAAs labeled with stable isotopes. This system is based on two thermostable enzymes: D-amino acid dehydrogenase, catalyzing NADPH-dependent enantioselective amination of 2-oxo acids to produce the corresponding D-amino acids, and glucose dehydrogenase, catalyzing NADPH regeneration from NADP(+) and D-glucose. After incubation with the enzymes for 2 h at 65°C and pH 10.5, 2-oxo-4-methylvaleric acid was converted to D-leucine with an excellent yield (>99 %) and optical purity (>99 %).
2.Formation of new polyhydroxyalkanoate containing 3-hydroxy-4-methylvalerate monomer in Burkholderia sp.
Lau NS1, Tsuge T, Sudesh K. Appl Microbiol Biotechnol. 2011 Mar;89(5):1599-609. doi: 10.1007/s00253-011-3097-6. Epub 2011 Jan 29.
Burkholderia sp. synthase has been shown to polymerize 3-hydroxybutyrate (3HB), 3-hydroxyvalerate, and 3-hydroxy-4-pentenoic acid monomers. This study was carried out to evaluate the ability of Burkholderia sp. USM (JCM 15050) and its transformant harboring the polyhydroxyalkanoate (PHA) synthase gene of Aeromonas caviae to incorporate the newly reported 3-hydroxy-4-methylvalerate (3H4MV) monomer. Various culture parameters such as concentrations of nutrient rich medium, fructose and 4-methylvaleric acid as well as harvesting time were manipulated to produce P(3HB-co-3H4MV) with different 3H4MV compositions. The structural properties of PHA containing 3H4MV monomer were investigated by using nuclear magnetic resonance and Fourier transform infrared spectroscopy (FTIR). The relative intensities of the bands at 1,183 and 1,228 cm⁻¹ in the FTIR spectra enabled the rapid detection and differentiation of P(3HB-co-3H4MV) from other types of PHA.
3.Branched-chain 2-oxoacid transamination increases GABA-shunt metabolism and insulin secretion in isolated islets.
Pizarro-Delgado J1, Hernández-Fisac I, Martín-Del-Río R, Tamarit-Rodriguez J. Biochem J. 2009 Apr 15;419(2):359-68. doi: 10.1042/BJ20081731.
We have previously shown that oxo-4-methylpentanoate promotes islet GABA (gamma-aminobutyric acid) metabolism and stimulates insulin secretion. The main aim of this work was to explore the participation of the transamination of branched-chain 2-oxoacids in these processes with the aid of several inhibitors of this enzyme activity. No correlation was found between the transamination of branched-chain 2-oxoacids in islet homogenates and insulin secretion. However, in vivo transamination rates correlated better with the secretion capacity of the different branched-chain 2-oxoacids. Gabapentin, a specific inhibitor of the cytosolic isoenzyme, showed greater potential to decrease the in vitro transamination rates of oxo-3-methylbutyrate and oxo-3-methylpentanoate than those of oxo-4-methylpentanoate and oxohexanoate; this correlated with its capacity to decrease insulin secretion. 4-Methylvaleric acid very strongly inhibited the transamination of all the branched-chain 2-oxoacids and blocked their capacity to decrease islet GABA and to stimulate insulin secretion.
4.Neural mechanisms of anhedonia in schizophrenia: a PET study of response to unpleasant and pleasant odors.
Crespo-Facorro B1, Paradiso S, Andreasen NC, O'Leary DS, Watkins GL, Ponto LL, Hichwa RD. JAMA. 2001 Jul 25;286(4):427-35.
CONTEXT: Loss of the capacity to experience pleasure (anhedonia) is a core clinical feature of schizophrenia. Although functional imaging techniques have been successful in identifying the neural basis of cognitive impairments in schizophrenia, no attempts to date have been made to investigate neural systems underlying emotional disturbances.