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MilliporeSigma

177504

Sigma-Aldrich

Hexadecanedioic acid

96%

Sinónimos:

Thapsic acid

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About This Item

Fórmula lineal:
HOOC(CH2)14COOH
Número de CAS:
Peso molecular:
286.41
Beilstein/REAXYS Number:
1792831
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

96%

mp

120-123 °C (lit.)

SMILES string

OC(=O)CCCCCCCCCCCCCCC(O)=O

InChI

1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)

InChI key

QQHJDPROMQRDLA-UHFFFAOYSA-N

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General description

Hexadecanedioic acid (HDDA), also known as thapsic acid, is a straight-chain aliphatic dicarboxylic acid with the molecular formula C₁₆H30O₄. It features two carboxylic acid groups (-COOH) at each end of a saturated hydrocarbon chain, which imparts thermal stability, hydrophobicity, and biocompatibility to the polymers.

Application

Hexadecanedioic acid can be used:
  • As a tracer (radiolabeled with Gallium-68), for cardiac metabolic imaging, enabling visualization of fatty acid metabolism in the heart during PET scans. Its biocompatibility and mimicry of natural fatty acid pathways enhance diagnostic assessments of cardiac function.
  • As a precursor to prepare noncross-linked terpolyester via melt polycondensation. This material can be used to fabricate ecofriendly food packaging materials.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Young-Jae You et al.
European journal of medicinal chemistry, 39(2), 189-193 (2004-02-28)
Esters of 4'-demethyl-4-deoxypodophyllotoxin (DDPT) with alkanoic acids and alkanedioic acids were prepared and tested for cytotoxic and antitumor activity. Among 19 esters, esters of propanoic acid, tetradecanedioic acid, 13-carboxyundecanoic acid, and hexadecanedioic acid improved the antitumor activity compared with that
A Aarsland et al.
Journal of lipid research, 30(11), 1711-1718 (1989-11-01)
Previous work in this laboratory indicated that sulfur-substituted fatty acid analogues, 1.10-bis(carboxymethylthio)decane and alkylthioacetic acid, both non-beta-oxidizable compounds, and the beta-oxidizable alkylthiopropionic acid (1) caused, to different extents, dose-related hepatomegaly and proliferation of peroxisomes and enhanced peroxisomal fatty acid beta-oxidation.
N Shirane et al.
Biochemistry, 32(49), 13732-13741 (1993-12-14)
Cytochrome P450BM-3 preferentially oxidized fatty acids with terminal double or triple bonds to the omega-2 hydroxylated fatty acids rather than, respectively, to the epoxide or diacid metabolites. The enzyme is inactivated during catalytic turnover of long, terminally unsaturated fatty acids
Anupam Mathur et al.
Bioorganic & medicinal chemistry, 16(17), 7927-7931 (2008-08-15)
Development of a (99m)Tc-fatty acid analogue is of interest, as (99m)Tc is logistically advantageous over the cyclotron-produced (11)C and (123)I. Synthesis of a 16 carbon fatty acid derivative and its radiolabeling with the novel [(99m)TcN(PNP)](2+) core is described here. Hexadecanedioic
Vukic Soskic et al.
Journal of proteome research, 5(12), 3453-3458 (2006-12-02)
Serum and plasma are the major sources of human material for clinical molecular diagnostics and drug discovery. However, due to the high abundance of some proteins, of which serum albumin (SA) is most prominent, lower-abundance proteins often remain undetectable in

Global Trade Item Number

Número de referencia del producto (SKU)GTIN
177504-1G4061826661635
177504-250MG
177504-5G4061838753250

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