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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:
503-49-1
Molecular Weight:
162.14
Beilstein:
1769194
EC Number:
207-971-1
MDL number:
MFCD00002712
UNSPSC Code:
12352100
PubChem Substance ID:
57654253
NACRES:
NA.22

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

H4392-BULK:
H4392-100MG:
H4392-1G:
H4392-500MG:
H4392-5G:
H4392-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jan Frank et al.
The British journal of nutrition, 92(1), 169-176 (2004-07-03)
Secoisolariciresinol diglucoside (SDG) is an important dietary lignan that is found at very high levels in flaxseed (1-4 %, w/w). Flaxseed lignans have received much research interest in recent years because of reported phyto-oestrogenic, anticarcinogenic, and anti-atherogenic effects. Previously, flaxseed
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
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
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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