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503-49-1,MFCD00002712
Catalog No.:AA00I8Y6

503-49-1 | 3-Hydroxy-3-methylglutaric acid

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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I8Y6
Chemical Name:
3-Hydroxy-3-methylglutaric acid
CAS Number:
503-49-1
Molecular Formula:
C6H10O5
Molecular Weight:
162.1406
MDL Number:
MFCD00002712
SMILES:
OC(=O)CC(CC(=O)O)(O)C
Properties
Properties
 
BP:
414.3°C at 760 mmHg  
Form:
Solid  
MP:
105-108 °C(lit.)  
Refractive Index:
1.4230 (estimate)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
158  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
4  
XLogP3:
-1.2  

Downstream Synthesis Route

[1]Tschesche,R.;Machleidt,H.[JustusLiebigsAnnalenderChemie,1960,vol.631,p.61-76]

[2]Tschesche,R.;Machleidt,H.[JustusLiebigsAnnalenderChemie,1960,vol.631,p.61-76]

[3]Kawasaki,Motoji;Matsuda,Fuyuhiko;Terashima,Shiro[Tetrahedron,1988,vol.44,#18,p.5727-5744]

[4]Bardshiri,Esfandiar;Simpson,ThomasJ.;Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.PerkintransactionsI,1984,#8,p.1765-1767]Bollerner,Yu.S.;Abdullaev,N.D.;Gorovits,M.B.;Abubakirov,N.K.[ChemistryofNaturalCompounds,1983,vol.19,#3,p.186-190][KhimiyaPrirodnykhSoedinenii,1983,vol.19,#3,p.197-201]Mizutani,Kenji;Yuda,Masamichi;Tanaka,Osamu;Saruwatari,Yuh-ichiro;Jia,Ming-Ru;etal.[Chemicalandpharmaceuticalbulletin,1988,vol.36,#7,p.2726-2729]Zhang,Lian-Ying;Hamberg,Mats[ChemistryandPhysicsofLipids,1994,vol.74,#2,p.151-161]

[5]Lewer,Paul;MacMillan,Jake[JournaloftheChemicalSociety.PerkintransactionsI,1983,#7,p.1417-1420]

[1]Walker,PaulD.;Williams,Christopher;Weir,AngusN.M.;Wang,Luoyi;Crosby,John;Race,PaulR.;Simpson,ThomasJ.;Willis,ChristineL.;Crump,MatthewP.[AngewandteChemie-InternationalEdition,2019,vol.58,#36,p.12446-12450][Angew.Chem.,2019,vol.131,#36,p.12576-12580]

[2]Klostermann;Smith[JournaloftheAmericanChemicalSociety,1954,vol.76,p.1229]

[3]Sorokin[JournalfurpraktischeChemie(Leipzig1954),1881,vol.<2>23,p.276]

[4]Tschesche,R.;Machleidt,H.[JustusLiebigsAnnalenderChemie,1960,vol.631,p.61-76]Rabinowitz[BiochemicalPreparations,1958,vol.6,p.25]

[5]Ahmed,SalmanA.;Bardshiri,Esfandiar;Simpson,ThomasJ.[TetrahedronLetters,1988,vol.29,#13,p.1595-1596]

[6]Kawasaki,Motoji;Matsuda,Fuyuhiko;Terashima,Shiro[Tetrahedron,1988,vol.44,#18,p.5727-5744]

[7]Bardshiri,Esfandiar;Simpson,ThomasJ.;Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.PerkintransactionsI,1984,#8,p.1765-1767]

[8]Lewer,Paul;MacMillan,Jake[JournaloftheChemicalSociety.PerkintransactionsI,1983,#7,p.1417-1420]

[9]Baran;Laos;Langford;Miller;Jett;Taite;Rohrbacher[JournalofMedicinalChemistry,1985,vol.28,#5,p.597-601]

[10]Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.Chemicalcommunications,1980,#9,p.400-401]

[11]Ahmed,SalmanA.;Bardshiri,Esfandiar;Simpson,ThomasJ.[JournaloftheChemicalSociety.Chemicalcommunications,1987,p.883-884]

[1]Walker,PaulD.;Williams,Christopher;Weir,AngusN.M.;Wang,Luoyi;Crosby,John;Race,PaulR.;Simpson,ThomasJ.;Willis,ChristineL.;Crump,MatthewP.[AngewandteChemie-InternationalEdition,2019,vol.58,#36,p.12446-12450][Angew.Chem.,2019,vol.131,#36,p.12576-12580]

[2]Brown,Kenneth;Devlin,J.Alastair;Robins,DavidJ.[JournaloftheChemicalSociety.PerkintransactionsI,1983,#8,p.1819-1824]

[3]Hilzetal.[BiochemischeZeitschrift,1958,vol.329,p.476,484]

[4]Bardshiri,Esfandiar;Simpson,ThomasJ.;Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.PerkintransactionsI,1984,#8,p.1765-1767]

[5]Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.Chemicalcommunications,1980,#9,p.400-401]

[6]Hashimoto,Kimiko;Kitaguchi,Jun-Ichi;Mizuno,Yasuhiro;Kobayashi,Tadao;Shirahama,Haruhisa[TetrahedronLetters,1996,vol.37,#13,p.2275-2278]

[7]Bardshiri,Esfandiar;Simpson,ThomasJ.;Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.PerkintransactionsI,1984,#8,p.1765-1767]

[1]Adams;VanDuuren[JournaloftheAmericanChemicalSociety,1953,vol.75,p.2377]

[1]Ahmed,SalmanA.;Bardshiri,Esfandiar;McIntyre,C.Rupert;Simpson,ThomasJ.[AustralianJournalofChemistry,1992,vol.45,#1,p.249-274]

[2]Adams;VanDuuren[JournaloftheAmericanChemicalSociety,1953,vol.75,p.2377]

[3]Ahmed,SalmanA.;Bardshiri,Esfandiar;Simpson,ThomasJ.[TetrahedronLetters,1988,vol.29,#13,p.1595-1596]Ahmed,SalmanA.;Bardshiri,Esfandiar;Simpson,ThomasJ.[JournaloftheChemicalSociety.Chemicalcommunications,1987,p.883-884]

[4]Bardshiri,Esfandiar;Simpson,ThomasJ.;Scott,A.Ian;Shishido,Kozo[JournaloftheChemicalSociety.PerkintransactionsI,1984,#8,p.1765-1767]

[5]Zhang,Lian-Ying;Hamberg,Mats[ChemistryandPhysicsofLipids,1994,vol.74,#2,p.151-161]

Literature

Title: Flavonol glycosides acylated with 3-hydroxy-3-methylglutaric acid as systematic characters in Rosa.

Journal: Phytochemistry 20120901

Title: Gymnopilin--a substance produced by the hallucinogenic mushroom, Gymnopilus junonius--mobilizes intracellular Ca(2+) in dorsal root ganglion cells.

Journal: Biomedical research (Tokyo, Japan) 20120401

Title: Pharmacogenetics meets metabolomics: discovery of tryptophan as a new endogenous OCT2 substrate related to metformin disposition.

Journal: PloS one 20120101

Title: Cholesterol-lowering probiotics as potential biotherapeutics for metabolic diseases.

Journal: Experimental diabetes research 20120101

Title: Multiple effects of gymnopilin on circulatory system of the rat.

Journal: Biological & pharmaceutical bulletin 20120101

Title: Presence of caffeic acid in flaxseed lignan macromolecule.

Journal: Plant foods for human nutrition (Dordrecht, Netherlands) 20110901

Title: Neurochemical evidence that 3-methylglutaric acid inhibits synaptic Na+,K+-ATPase activity probably through oxidative damage in brain cortex of young rats.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20110201

Title: Carboxylated hyperbranched poly(glycidol)s for preparation of pH-sensitive liposomes.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20110105

Title: Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix.

Journal: Journal of natural products 20101129

Title: Differential HMG-CoA lyase expression in human tissues provides clues about 3-hydroxy-3-methylglutaric aciduria.

Journal: Journal of inherited metabolic disease 20100801

Title: Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.

Journal: The Plant journal : for cell and molecular biology 20100601

Title: Inhibition of antigen-induced degranulation by aryl compounds isolated from the bark of Betula platyphylla in RBL-2H3 cells.

Journal: Bioorganic & medicinal chemistry letters 20100501

Title: [Late onset 3-HMG-CoA lyase deficiency: a rare but treatable disorder].

Journal: Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20100101

Title: Striatum is more vulnerable to oxidative damage induced by the metabolites accumulating in 3-hydroxy-3-methylglutaryl-CoA lyase deficiency as compared to liver.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20090601

Title: Ten novel HMGCL mutations in 24 patients of different origin with 3-hydroxy-3-methyl-glutaric aciduria.

Journal: Human mutation 20090301

Title: The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides.

Journal: Phytochemistry 20090101

Title: Anti-microtubule activity of tubeimoside I and its colchicine binding site of tubulin.

Journal: Cancer chemotherapy and pharmacology 20080901

Title: Induction of oxidative stress by the metabolites accumulating in 3-methylglutaconic aciduria in cerebral cortex of young rats.

Journal: Life sciences 20080312

Title: Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex.

Journal: Journal of neuroscience research 20080215

Title: 3-Methylglutaric acid as a 13C solid-state NMR standard.

Journal: Solid state nuclear magnetic resonance 20061001

Title: NMR spectroscopic studies on the late onset form of 3-methylglutaconic aciduria type I and other defects in leucine metabolism.

Journal: NMR in biomedicine 20060401

Title: Metabolomic and bioinformatic analyses in asphyxiated neonates.

Journal: Clinical biochemistry 20060301

Title: A single-residue mutation, G203E, causes 3-hydroxy-3-methylglutaric aciduria by occluding the substrate channel in the 3D structural model of HMG-CoA lyase.

Journal: Journal of inherited metabolic disease 20060201

Title: Flax lignans--analytical methods and how they influence our lunderstanding of biological activity.

Journal: Journal of AOAC International 20060101

Title: Hypocholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed.

Journal: Atherosclerosis 20050401

Title: Molecular docking of the highly hypolipidemic agent alpha-asarone with the catalytic portion of HMG-CoA reductase.

Journal: Bioorganic & medicinal chemistry letters 20050215

Title: Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.

Journal: The British journal of nutrition 20040701

Title: Fungal metabolic model for 3-methylcrotonyl-CoA carboxylase deficiency.

Journal: The Journal of biological chemistry 20040206

Title: Molecular basis of 3-hydroxy-3-methylglutaric aciduria.

Journal: Journal of physiology and biochemistry 20031201

Title: Structural (betaalpha)8 TIM barrel model of 3-hydroxy-3-methylglutaryl-coenzyme A lyase.

Journal: The Journal of biological chemistry 20030801

Title: Biochemical and molecular analyses in three patients with 3-hydroxy-3-methylglutaric aciduria.

Journal: Journal of inherited metabolic disease 20030101

Title: 3-methyglutaconic aciduria in a Chinese patient with glycogen storage disease Ib.

Journal: Journal of inherited metabolic disease 20030101

Title: Immunoglobulins and cytokines level in follicular fluid in relation to etiology of infertility and their relevance to IVF outcome.

Journal: American journal of reproductive immunology (New York, N.Y. : 1989) 20020201

Title: An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues.

Journal: Phytochemistry 20011001

Title: 3-Hydroxy-3-methylglutaric aciduria in an Italian patient is caused by a new nonsense mutation in the HMGCL gene.

Journal: Molecular genetics and metabolism 20010701

Title: Mitochondrial DNA depletion associated with partial complex II and IV deficiencies and 3-methylglutaconic aciduria.

Journal: Journal of child neurology 20010201

Title: 3-Alkyl-3-hydroxyglutaric acids: a new class of hypocholesterolemic HMG CoA reductase inhibitors. 1.

Journal: Journal of medicinal chemistry 19850501

Title: Effect in vitro of 3-hydroxy-3-methylglutaric acid on the synthesis of mevalonate and its precursors.

Journal: Archives internationales de physiologie et de biochimie 19770201

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Tags:503-49-1 Molecular Formula|503-49-1 MDL|503-49-1 SMILES|503-49-1 3-Hydroxy-3-methylglutaric acid