Parthenolide

Parthenolide
Names
	IUPAC name (1aR,4E,7aS,10aS,10bR)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Identifiers
CAS Number	20554-84-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL540445 ;
ChemSpider	20126246 ;
ECHA InfoCard	100.220.558
PubChem CID	5420805;
RTECS number	LY4220000;
UNII	2RDB26I5ZB ;
CompTox Dashboard (EPA)	DTXSID2040579 ;
	InChI InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 Key: KTEXNACQROZXEV-SLXBATTESA-N ; Key: KTEXNACQROZXEV-SLXBATTEBY; InChI=1/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1;
	SMILES C/C/1=C\CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C;
Properties
Chemical formula	C15H20O3
Molar mass	248.322 g·mol−1
Melting point	113 to 115 °C (235 to 239 °F; 386 to 388 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare).^[1] It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.^[2]^[3]

Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug.

References

↑ Onozato, Thelma; Nakamura, Celso Vataru; Garcia Cortez, Diógenes Aparício; Dias Filho, Benedito Prado; Ueda-Nakamura, Tânia (2009). "Tanacetum vulgare: antiherpes virus activity of crude extract and the purified compound parthenolide". Phytother Res. 23 (6): 791–6. doi:10.1002/ptr.2638. PMID 19152371. S2CID 3547899.
↑ Quick, Andrew; Rogers, Donald (1976). "Crystal and molecular structure of parthenolide [4,5-epoxygermacra-1(10),11(13)-dien-12,6-olactone]". Journal of the Chemical Society, Perkin Transactions 2 (4): 465. doi:10.1039/p29760000465. ISSN 0300-9580.
↑ Long, Jing; Ding, Ya-Hui; Wang, Pan-Pan; Zhang, Quan; Chen, Yue (2013-10-18). "Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl Analogue". The Journal of Organic Chemistry. 78 (20): 10512–10518. doi:10.1021/jo401606q. ISSN 0022-3263. PMID 24047483.

[1] Onozato, Thelma; Nakamura, Celso Vataru; Garcia Cortez, Diógenes Aparício; Dias Filho, Benedito Prado; Ueda-Nakamura, Tânia (2009). "Tanacetum vulgare: antiherpes virus activity of crude extract and the purified compound parthenolide". Phytother Res. 23 (6): 791–6. doi:10.1002/ptr.2638. PMID 19152371. S2CID 3547899.

[2] Quick, Andrew; Rogers, Donald (1976). "Crystal and molecular structure of parthenolide [4,5-epoxygermacra-1(10),11(13)-dien-12,6-olactone]". Journal of the Chemical Society, Perkin Transactions 2 (4): 465. doi:10.1039/p29760000465. ISSN 0300-9580.

[3] Long, Jing; Ding, Ya-Hui; Wang, Pan-Pan; Zhang, Quan; Chen, Yue (2013-10-18). "Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl Analogue". The Journal of Organic Chemistry. 78 (20): 10512–10518. doi:10.1021/jo401606q. ISSN 0022-3263. PMID 24047483.

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References