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M5693

Sigma-Aldrich

MEDICA 16

powder, ≥97% (HPLC)

Synonym(s):

3,3,14,14-Tetramethylhexadecanedioic acid

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About This Item

Empirical Formula (Hill Notation):
C20H38O4
CAS Number:
87272-20-6
Molecular Weight:
342.51
MDL number:
MFCD00797684
UNSPSC Code:
12352200
PubChem Substance ID:
24724539
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

mp

154-159 °C

solubility

DMSO: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(C)(CCCCCCCCCCC(C)(C)CC(O)=O)CC(O)=O

InChI

1S/C20H38O4/c1-19(2,15-17(21)22)13-11-9-7-5-6-8-10-12-14-20(3,4)16-18(23)24/h5-16H2,1-4H3,(H,21,22)(H,23,24)

InChI key

HYSMCRNFENOHJH-UHFFFAOYSA-N

Biochem/physiol Actions

MEDICA 16 is an ATP-citrate lyase inhibitor and potent triacylglycerol-lowering agent. The product is hypolipidemic, antidiabetic, and shows reduced adiposity.

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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N Mayorek et al.
Diabetes, 46(12), 1958-1964 (1997-12-10)
Beta,beta'-methyl-substituted hexadecanedioic acid (MEDICA 16) consists of a nonmetabolizable long-chain fatty acid designed to probe the effect exerted by fatty acids on insulin sensitivity. The effect of MEDICA 16 was evaluated in insulin-resistant Zucker (fa/fa) rats in terms of liver
R Hertz et al.
The Journal of biological chemistry, 270(22), 13470-13475 (1995-06-02)
The hypolipidemic effect exerted by beta,beta'-tetramethyl-hexadecanedioic acid (Medica 16) is accounted for by enhanced catabolism of plasma triglyceride-rich lipoproteins due to a decrease in plasma apolipoprotein C-III (Frenkel, B., Mayorek, N., Hertz, R., and Bar-Tana, J. (1988) J. Biol. Chem.
R Brandes et al.
Biochemical pharmacology, 50(11), 1949-1951 (1995-11-27)
Nonmetabolizable fatty acids are shown here to induce adipose conversion of 3T3-L1 preadipocytes as well as to activate transcription of a reporter plasmid promoted by a peroxisome proliferators response element. This dual activity was also observed using the peroxisome proliferator
Qi Sun et al.
Molecular pharmacology, 78(5), 804-810 (2010-08-06)
GPR120 is a G protein-coupled receptor expressed preferentially in the intestinal tract and adipose tissue, that has been implicated in mediating free fatty acid-stimulated glucagon-like peptide-1 (GLP-1) secretion. To develop GPR120-specific agonists, a series of compounds (denoted as NCG compounds)
T N Wells et al.
European journal of biochemistry, 204(1), 249-255 (1992-02-15)
In thiol redox buffers at pH 8.0, rat liver ATP-citrate lyase is in equilibrium between an oxidised inactive form and a reduced active form. The reduced enzyme is inactivated by oxidised glutathione (GSSG) at a rate of 45 min-1.M-1 and
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