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Capillin

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Capillin
Names
Preferred IUPAC name 1-Phenylhexa-2,4-diyn-1-one
Other names Capillin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H8O/c1-2-3-5-10-12(13)11-8-6-4-7-9-11/h4,6-9H,1H3Key: RAZOKRUZEQERLH-UHFFFAOYSA-N
SMILES
  • CC#CC#CC(=O)C1=CC=CC=C1
Properties
Chemical formula C12H8O
Molar mass 168.195 g·mol
Melting point 82–83 °C
Solubility in water 0.0177 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Capillin is a naturally occurring organic compound with the chemical formula C
12H
8O. The structure contains acetophenone and a polyyne (pentadiynyl) portion, conjugated together as an ynone.

Chemical taxonomy

Capillin is found in the essential oil of a number of Artemisia species, including Artemisia monosperma and Artemisia dracunculus (tarragon). The substance was initially isolated from Artemisia capillaris in 1956.

Applications

Capillin is a biologically active substance. It has strong antifungal activity, and it is possibly antitumoral. Capillin exhibits cytotoxic activity and could cause apoptosis of certain human tumor cells.

References

  1. Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk. "Showing metabocard for Capillin (HMDB32867)". Human Metabolome Database, HMDB. 5.0.
  2. Nash, B. W.; Thomas, D. A.; Warburton, W. K.; Williams, Thelma D. (1965). "535. The preparation of capillin and some related compounds, and of some substituted pent-4-en-2-yn-1-ones". J. Chem. Soc.: 2983–2988. doi:10.1039/JR9650002983.
  3. Whelan LC, Ryan MF (2004). "Effects of the polyacetylene capillin on human tumour cell lines". Anticancer Research. 24 (4): 2281–6. PMID 15330173.
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