3-Hydroxy-3-methylglutaric acid is a dicarboxylic acid, characterized by a glutaric acid molecule where one of the two hydrogen atoms at position 3 is replaced by a hydroxyl group and the other by a methyl group. It has been found to accumulate in the urine of patients with HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It is found in Crotalaria dura, a plant metabolite. 3-Hydroxy-3-methylglutaric acid has multiple functions, including as an antimetabolite, a cholesterol-lowering drug, an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, a human metabolite, and a plant metabolite. It is a dicarboxylic acid, a 3-hydroxycarboxylic acid, and a tertiary alcohol, functionally related to glutaric acid. It is the conjugate acid of 3-hydroxy-3-methylglutaric acid (1-). It is a lipid-lowering drug that reduces cholesterol, triglycerides, serum β-lipoprotein, and phospholipid levels. Its mechanism of action involves interfering with the enzymatic step of acetic acid conversion to hydroxymethylglutaryl-CoA and inhibiting the activity of hydroxymethylglutaryl-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis. Meglucopyll has been reported in Drosophila melanogaster, Piper longum, and other organisms with relevant data. 3-Hydroxymethylglutaryl acid is a metabolite that accumulates in the urine of patients with 3-hydroxy-3-methylglutaryluria (a rare congenital metabolic defect, OMIM 246450). 3-Hydroxy-3-methylglutaryluria is caused by reduced activity of mitochondrial 3-hydroxy-3-methylglutaryl-CoA lyase (EC 4.1.3.4). This enzyme catalyzes the final step in the degradation of leucine and plays a crucial role in ketone body formation. Its urinary organic acid profile differs from other known leucine degradation defects (such as maple syrup urine disease (OMIM 248600), isovaleric acidemia (OMIM 243500), and methylcrotonylglycinemia (OMIM 210200)). Clinical manifestations include hepatomegaly, lethargy or coma, and respiratory arrest. Biochemical tests show that the disease is characterized by ketosis, accompanied by hypoglycemia, acidosis, elevated transaminases, and varying degrees of hyperammonemia. The urinary organic acid profile shows elevated concentrations of 3-hydroxy-3-isovaleric acid, 3-hydroxy-3-methylglutaric acid, 3-methylglutaric acid, and 3-methylglutaric acid (A3352, A3353, A3354). A lipid-lowering drug can reduce cholesterol, triglycerides, serum β-lipoprotein, and phospholipid levels. Its mechanism of action is to interfere with the enzymatic step of acetic acid conversion to hydroxymethylglutaryl-CoA and to inhibit the activity of hydroxymethylglutaryl-CoA reductase, which is the rate-limiting enzyme in cholesterol biosynthesis.

C6H10O5

162.14

162.053

503-49-1

Meglutol-d3;59060-36-5

1662

White to off-white solid powder

1.417 g/cm3

120 °C / 13mmHg

105-108 °C(lit.)

182.2ºC

1.512

-1.2

3

5

4

11

158

0

O([H])C(C([H])([H])[H])(C([H])([H])C(=O)O[H])C([H])([H])C(=O)O[H]

NPOAOTPXWNWTSH-UHFFFAOYSA-N

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

3-hydroxy-3-methylpentanedioic acid

NSC 361411; HMGA; Meglutol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~250 mg/mL (~1541.88 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (12.83 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 20.8 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.

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Solubility in Formulation 2: ≥ 2.08 mg/mL (12.83 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 20.8 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (12.83 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)