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H6132

Sigma-Aldrich

DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate

≥90% (HPLC)

Synonym(s):

HMG-CoA

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About This Item

Empirical Formula (Hill Notation):
C27H42N7Na2O20P3S · xH2O
CAS Number:
103476-21-7
Molecular Weight:
955.62 (anhydrous basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24895729
NACRES:
NA.51

Quality Level

200

Assay

≥90% (HPLC)

storage temp.

−20°C

SMILES string

O.[Na+].[Na+].CC(O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n2cnc3c(N)ncnc23

InChI

1S/C27H44N7O20P3S.2Na.H2O/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34;;;/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45);;;1H2/q;2*+1;/p-2/t14-,19-,20-,21-,25-,27?;;;/m1.../s1

InChI key

QGWMCHPRNDWWMT-UAUHQYJPSA-L

Related Categories

General description

DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is obtained from acetyl-CoA and acetoacetyl-CoA during condensation with the help of HMG-CoA synthase.

Application

DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate has been used in drug treatment to study its effect on mTORC1 regulation. It has also been used to compare the acylomes of two reactive acyl-CoA species, like HMG-CoA and glutaryl-CoA.

Biochem/physiol Actions

DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is a substrate used to study the specificity and kinetics of the enzyme 3-hydroxyl-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase. HMG-CoA is the key intermediate in the biosynthsis of terpenes and ketone bodies. Its metabolism is the target of statin drugs used to control cholesterol levels.
DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) acts as a precursor of cholesterol synthesis. Inhibition of HMG-CoA can decrease cholesterol synthesis. This can be converted to β-hydroxybutyrate in the blood. HMG-CoA is a regulatory enzyme for cholesterol biosynthesis, it couples with LDL receptor to regulate cholesterol synthesis, once it is inhibited it would decrease cholesterol synthesis.

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

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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Alex Pitcher et al.
American heart journal, 169(5), 605-612 (2015-05-13)
A number of randomized trials are underway, which will address the effects of angiotensin receptor blockers (ARBs) on aortic root enlargement and a range of other end points in patients with Marfan syndrome. If individual participant data from these trials
Distribution of Fatty Acids and Lipids During Pregnancy
Advances in Clinical Chemistry, 84, 209-239 (2018)
Rajakrishnan Veluthakal et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 39(6), 2110-2120 (2016-11-02)
At least 300 prenylated proteins are identified in the human genome; the majority of which partake in a variety of cellular processes including growth, differentiation, cytoskeletal organization/dynamics and vesicle trafficking. Aberrant prenylation of proteins is implicated in human pathologies including
Guixiang Zhang et al.
Protein expression and purification, 163, 105454-105454 (2019-07-14)
Pogostemon cablin is an important commercial source of patchouli oil, whose main active ingredient is patchouli alcohol. This sesquiterpene is a product of the mevalonate pathway, in which 3-hydroxy-3-methyl-glutaryl-coenzyme A reductase (HMGCR) is the rate-limiting enzyme. In this study, P.
Leucine Signals to mTORC1 via Its Metabolite Acetyl-Coenzyme A
Son SM, et al.
Cell Metabolism, 29(1), 192-201 (2019)
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Articles

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

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