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177504

Sigma-Aldrich

Hexadecanedioic acid

96%

Synonym(s):

Thapsic acid

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About This Item

Linear Formula:
HOOC(CH2)14COOH
CAS Number:
505-54-4
Molecular Weight:
286.41
Beilstein:
1792831
EC Number:
208-013-5
MDL number:
MFCD00002746
UNSPSC Code:
12162002
PubChem Substance ID:
24850364
NACRES:
NA.23

Quality Level

200

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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

177504-BULK:
177504-250MG:
177504-1G:
177504-5G:
177504-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB6881
BCBX0713
BCBV7084
BCBR9024V
BCBB1475V

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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
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