Capillin

Capillin
	source ↗
Names
	Preferred IUPAC name 1-Phenylhexa-2,4-diyn-1-one
	Other names Capillin
Identifiers
CAS Number	495-74-9 Y;
3D model (JSmol)	Interactive image;
ChemSpider	9899;
PubChem CID	10321;
UNII	9JXZ3SJG0I Y;
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 (180–181 °F; 355–356 K)
Solubility in water	0.0177 mg/mL
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1 mg/kg (IV, mice)
	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 toxic 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).² The substance was initially isolated from Artemisia capillaris in 1956.³

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.⁴

References

CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980, 8(2)(297), 1982
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.
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] CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980, 8(2)(297), 1982

[2] 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.

[3] 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.

[pmid15330173-4] 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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