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Sigma-Aldrich

6-Heptynoic acid

90%

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About This Item

Linear Formula:
HC≡C(CH2)4COOH
CAS Number:
30964-00-2
Molecular Weight:
126.15
Beilstein/REAXYS Number:
1747024
MDL number:
MFCD00239430
UNSPSC Code:
12352100
PubChem Substance ID:
24868034
NACRES:
NA.22

assay

90%

refractive index

n20/D 1.451 (lit.)

bp

93-94 °C/1 mmHg (lit.)

density

0.997 g/mL at 25 °C (lit.)

SMILES string

OC(=O)CCCCC#C

InChI

1S/C7H10O2/c1-2-3-4-5-6-7(8)9/h1H,3-6H2,(H,8,9)

InChI key

OFCPMJGTZUVUSM-UHFFFAOYSA-N

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General description

6-Heptynoic acid is an alkynoic acid with an acetylene bond. It undergoes condensation with various pyrroles to afford optical diverse fluorescent dyes with a terminal alkyne.

Application

6-Heptynoic acid may be used for the following syntheses:
  • alkyne functionalized Boradiazaindacenes (BODIPY)dyes
  • natural products epothilone B and D
  • hymenialdisine (HMD) and aldisine (AD) affinity resins
  • alkynyl esters

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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A novel catalyst with a cuboidal PdMo3S4 core for the cyclization of alkynoic acids to enol lactones.
Wakabayashi T, et al.
Angewandte Chemie (International Edition in English), 35(18), 2123-2124 (1996)
Yongqin Wan et al.
Chemistry & biology, 11(2), 247-259 (2004-05-05)
Hymenialdisine (HMD) is a sponge-derived natural product kinase inhibitor with nanomolar activity against CDKs, Mek1, GSK3beta, and CK1 and micromolar activity against Chk1. In order to explore the broader application of the pyrrolo[2,3-c]azepine skeleton of HMD as a general kinase
Lauren Ray et al.
Nature communications, 7, 13609-13609 (2016-12-22)
Type I modular polyketide synthases assemble diverse bioactive natural products. Such multienzymes typically use malonyl and methylmalonyl-CoA building blocks for polyketide chain assembly. However, in several cases more exotic alkylmalonyl-CoA extender units are also known to be incorporated. In all
Martijn Verdoes et al.
Bioorganic & medicinal chemistry letters, 17(22), 6169-6171 (2007-09-25)
The synthesis of three acetylene functionalized BODIPY dyes is described. These dyes are used to fluorescently modify an azido functionalized epoxomicin analogue employing the Huisgen 1,3-dipolar cycloaddition, resulting in a panel of fluorescent epoxomicin derived proteasome probes.
Mariano Walter Pertino et al.
Molecules (Basel, Switzerland), 19(2), 2523-2535 (2014-02-26)
Dehydroabietic acid (DHA) is a naturally occurring diterpene with different and relevant biological activities. Previous studies have shown that some DHA derivatives display antiproliferative activity. However, the reported compounds did not include triazole derivatives. Starting from DHA (8,11,13-abietatrien-18-oic acid), and
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