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Key Documents

H4392

Sigma-Aldrich

3-Hydroxy-3-methylglutaric acid

≥95%

Synonym(s):

3-Hydroxy-3-methylpentanedioic acid

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About This Item

Linear Formula:
HOC(CH3)(CH2CO2H)2
CAS Number:
Molecular Weight:
162.14
Beilstein:
1769194
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95%

mp

105-108 °C (lit.)

storage temp.

−20°C

SMILES string

CC(O)(CC(O)=O)CC(O)=O

InChI

1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)

InChI key

NPOAOTPXWNWTSH-UHFFFAOYSA-N

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Application

  • Improvement of the functional value of green soybean (edamame) using germination and tempe fermentation: A comparative metabolomics study.: This research enhances the functional value of green soybean through germination and fermentation, identifying metabolites including those derived from 3-Hydroxy-3-methylglutaric acid. It offers insights into food processing and nutritional biochemistry (Iman et al., 2023).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A Kamal-Eldin et al.
Phytochemistry, 58(4), 587-590 (2001-09-29)
A straight-chain oligomeric structure composed of five secoisolariciresinoldiglucoside (SDG) residues interconnected by four 3-hydroxy-3-methyl glutaric acid (HMGA) residues (molecular weight ca. 4000 Da) was assigned to the main lignan of flaxseed on the basis of nuclear magnetic resonance spectroscopy (NMR).
Alister D Muir
Journal of AOAC International, 89(4), 1147-1157 (2006-08-19)
Flaxseed (Linum usitatissimum L.) is a major source of dietary intake of lignans by virtue of the high concentrations (0.7-1.5%) that are present in the seed. The principal lignan present in flaxseed is secoisolariciresinol diglucoside (SDG), which occurs as a
S Funghini et al.
Molecular genetics and metabolism, 73(3), 268-275 (2001-07-20)
3-Hydroxy-3-methylglutaric aciduria is a rare autosomal recessive inborn error of metabolism caused by deficiency of the mitochondrial enzyme 3-hydroxy-3-methylglutaryl-CoA lyase (HMGCL). Up to now only a few mutations have been reported in the HMGCL gene. We report the first Italian
Elaine A Porter et al.
Phytochemistry, 81, 90-96 (2012-06-23)
LC-UV-MS/MS analysis of leaf extracts from 146 accessions of 71 species of Rosa revealed that some taxa accumulated flavonol O-glycosides acylated with 3-hydroxy-3-methylglutaric acid, which are relatively uncommon in plants. The structures of two previously unrecorded examples isolated from Rosa
C Mir et al.
Journal of inherited metabolic disease, 29(1), 64-70 (2006-04-08)
3-Hydroxy-3-methylglutaric aciduria is a rare autosomal recessive genetic disorder that affects ketogenesis and leucine metabolism. The disease is caused by mutations in the gene coding for 3-hydroxy-3-methylglutaryl-coenzyme A lyase (HL). To date 26 different mutations have been described. A (betaalpha)(8)

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