Capillin

Capillin
Names
	Preferred IUPAC name 1-Phenylhexa-2,4-diyn-1-one
	Other names Capillin
Identifiers
CAS Number	495-74-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	9899;
PubChem CID	10321;
UNII	9JXZ3SJG0I ;
CompTox Dashboard (EPA)	DTXSID90197812 ;
	InChI InChI=1S/C12H8O/c1-2-3-5-10-12(13)11-8-6-4-7-9-11/h4,6-9H,1H3 Key: RAZOKRUZEQERLH-UHFFFAOYSA-N;
	SMILES CC#CC#CC(=O)C1=CC=CC=C1;
Properties
Chemical formula	C12H8O
Molar mass	168.195 g·mol−1
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 [77 °F], 100 kPa).
	Infobox references

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).^[1] The substance was initially isolated from Artemisia capillaris in 1956.^[2]

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.^[3]

References[]

^ Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel; Li, Carin; Karu, Naama; Sayeeda, Zinat; Lo, Elvis; Assempour, Nazanin; Berjanskii, Mark; Singhal, Sandeep; Arndt, David; Liang, Yonjie; Badran, Hasan; Grant, Jason; Serra Cayuela, Arnau; Liu, Yifeng; Mandal, Rupa; Neveu, Vanessa; Pon, Allison; Knox, Craig; Wilson, Michael; Manach, Claudine; Scalbert, Augustin. "Showing metabocard for Capillin (HMDB32867)". Human Metabolome Database, HMDB. 4.0.
^ 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.
^ Whelan LC, Ryan MF (2004). "Effects of the polyacetylene capillin on human tumour cell lines". Anticancer Research. 24 (4): 2281–6. PMID 15330173.

[1] Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel; Li, Carin; Karu, Naama; Sayeeda, Zinat; Lo, Elvis; Assempour, Nazanin; Berjanskii, Mark; Singhal, Sandeep; Arndt, David; Liang, Yonjie; Badran, Hasan; Grant, Jason; Serra Cayuela, Arnau; Liu, Yifeng; Mandal, Rupa; Neveu, Vanessa; Pon, Allison; Knox, Craig; Wilson, Michael; Manach, Claudine; Scalbert, Augustin. "Showing metabocard for Capillin (HMDB32867)". Human Metabolome Database, HMDB. 4.0.

[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.

[pmid15330173-3] 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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