Clovamide

Clovamide
	; cis-Clovamide
	; trans-Clovamide
Names
	IUPAC name (2S)-3-(3,4-Dihydroxyphenyl)-2-[[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
	Other names N-Caffeoyl-L-DOPA
Identifiers
CAS Number	53755-03-6 (cis) ; 53755-02-5 (trans) ;
3D model (JSmol)	Interactive image;
ChemSpider	4947752;
PubChem CID	6443790;
UNII	WZC65G68KW (cis) ; 973626KV9L (trans) ;
	InChI InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1 Key: GPZFXSWMDFBRGS-RYBZSIHZSA-N; InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1 Key: GPZFXSWMDFBRGS-RYBZSIHZBZ;
	SMILES c1cc(c(cc1C[C@@H](C(=O)O)NC(=O)/C=C\c2ccc(c(c2)O)O)O)O;
Properties
Chemical formula	C18H17NO7
Molar mass	359.334 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Clovamide is a chemical compound found in cacao.^[1]^[2] It has only been found in small amounts.^[3] It is also found in Trifolium pratense (red clover).^[4]

Clovamide can exist as either the cis- or trans- isomer.

In isolated neuroblastoma cells, clovamide has in vitro neuroprotective effects.^[5]

References

^ Sanbongi, Chiaki; Osakabe, Naomi; Natsume, Midori; Takizawa, Toshio; Gomi, Shuichi; Osawa, Toshihiko (1998). "Antioxidative Polyphenols Isolated from Theobromacacao". Journal of Agricultural and Food Chemistry. 46 (2): 454–457. doi:10.1021/jf970575o. PMID 10554262.
^ Arlorio, Marco; Locatelli, Monica; Travaglia, Fabiano; Coïsson, Jean-Daniel; Grosso, Erika Del; Minassi, Alberto; Appendino, Giovanni; Martelli, Aldo (2008). "Roasting impact on the contents of clovamide (N-caffeoyl-L-DOPA) and the antioxidant activity of cocoa beans (Theobroma cacao L.)". Food Chemistry. 106 (3): 967–975. doi:10.1016/j.foodchem.2007.07.009.
^ Caballero, B.; Finglas, P.; Toldrรก, F. (2015). Encyclopedia of Food and Health. Elsevier Science. p. 189. ISBN 978-0-12-384953-3.
^ Induction of clovamide by jasmonic acid in red clover. Tebayashi S, Ishihara A, Tsuda M and Iwamura H, Phytochemistry, 2000 Jun, 54(4), pages 387-392, PMID 10897479
^ Fallarini, S.; Miglio, G.; Paoletti, T.; Minassi, A.; Amoruso, A.; Bardelli, C.; Brunelleschi, S.; Lombardi, G. (2009). "Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death". British Journal of Pharmacology. 157 (6): 1072–1084. doi:10.1111/j.1476-5381.2009.00213.x. PMC 2737666. PMID 19466982.

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[1] Sanbongi, Chiaki; Osakabe, Naomi; Natsume, Midori; Takizawa, Toshio; Gomi, Shuichi; Osawa, Toshihiko (1998). "Antioxidative Polyphenols Isolated from Theobromacacao". Journal of Agricultural and Food Chemistry. 46 (2): 454–457. doi:10.1021/jf970575o. PMID 10554262.

[2] Arlorio, Marco; Locatelli, Monica; Travaglia, Fabiano; Coïsson, Jean-Daniel; Grosso, Erika Del; Minassi, Alberto; Appendino, Giovanni; Martelli, Aldo (2008). "Roasting impact on the contents of clovamide (N-caffeoyl-L-DOPA) and the antioxidant activity of cocoa beans (Theobroma cacao L.)". Food Chemistry. 106 (3): 967–975. doi:10.1016/j.foodchem.2007.07.009.

[Caballero_Finglas_Toldrรก_2015_p._1-PA189-3] Caballero, B.; Finglas, P.; Toldrรก, F. (2015). Encyclopedia of Food and Health. Elsevier Science. p. 189. ISBN 978-0-12-384953-3.

[4] Induction of clovamide by jasmonic acid in red clover. Tebayashi S, Ishihara A, Tsuda M and Iwamura H, Phytochemistry, 2000 Jun, 54(4), pages 387-392, PMID 10897479

[5] Fallarini, S.; Miglio, G.; Paoletti, T.; Minassi, A.; Amoruso, A.; Bardelli, C.; Brunelleschi, S.; Lombardi, G. (2009). "Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death". British Journal of Pharmacology. 157 (6): 1072–1084. doi:10.1111/j.1476-5381.2009.00213.x. PMC 2737666. PMID 19466982.

[1]

[2]

[3]

[4]

[5]

Names
cis-Clovamide
trans-Clovamide
IUPAC name (2S)-3-(3,4-Dihydroxyphenyl)-2-[[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
Other names N-Caffeoyl-L-DOPA
Identifiers
CAS Number	53755-03-6 (cis)^Y 53755-02-5 (trans)^Y
3D model (JSmol)	Interactive image
ChemSpider	4947752
PubChem CID	6443790
UNII	WZC65G68KW (cis)^Y 973626KV9L (trans)^Y
InChI InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1 Key: GPZFXSWMDFBRGS-RYBZSIHZSA-N InChI=1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1 Key: GPZFXSWMDFBRGS-RYBZSIHZBZ
SMILES c1cc(c(cc1C[C@@H](C(=O)O)NC(=O)/C=C\c2ccc(c(c2)O)O)O)O
Properties
Chemical formula	C₁₈H₁₇NO₇
Molar mass	359.334 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Clovamide

See also

References