Chlorophyllin

Chlorophyllin
Names
	Other names Natural green 3, E141
Identifiers
CAS Number	11006-34-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4586363 ;
ECHA InfoCard	100.031.117
PubChem CID	5479494;
UNII	1D276TYV9O ;
CompTox Dashboard (EPA)	DTXSID1045956 ;
	InChI InChI=1S/C34H36N4O6/c1-7-19-15(3)23-12-25-17(5)21(9-10-29(39)40)32(37-25)22(11-30(41)42)33-31(34(43)44)18(6)26(38-33)14-28-20(8-2)16(4)24(36-28)13-27(19)35-23/h7,12-14,17,21,35-36H,1,8-11H2,2-6H3,(H,39,40)(H,41,42)(H,43,44)/b23-12-,24-13-,25-12-,26-14-,27-13-,28-14-,32-22-,33-22-/t17-,21-/m0/s1 Key: OYINILBBZAQBEV-HHGNVTQFSA-N ; InChI=1/C34H36N4O6/c1-7-19-15(3)23-12-25-17(5)21(9-10-29(39)40)32(37-25)22(11-30(41)42)33-31(34(43)44)18(6)26(38-33)14-28-20(8-2)16(4)24(36-28)13-27(19)35-23/h7,12-14,17,21,35-36H,1,8-11H2,2-6H3,(H,39,40)(H,41,42)(H,43,44)/b23-12-,24-13-,25-12-,26-14-,27-13-,28-14-,32-22-,33-22-/t17-,21-/m0/s1 Key: OYINILBBZAQBEV-HHGNVTQFBL;
	SMILES CCC1=CC2=NC1=CC3=C(C4=C(C(C(=C4[N-]3)C5=NC(=CC6=NC(=C2)C(=C6C)C=C)C(C5CCC(=O)[O-])C)C(=O)[O-])[O-])C.[Cu+2].[Cu+2];
Properties
Chemical formula	C34H31CuN4Na3O6
Molar mass	724.159 g·mol−1
	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

Chlorophyllin refers to any one of a group of closely related water-soluble salts that are semi-synthetic derivatives of chlorophyll, differing in the identity of the cations associated with the anion. Its most common form is a sodium/copper derivative used as a food additive and in alternative medicine. As a food coloring agent, copper complex chlorophyllin is known as natural green 3 and has the E number E141.^[1]

Uses

Alternative medicine

Chlorophyllin is the active ingredient in a number of internally taken preparations^{[medical citation needed]} intended to reduce odors associated with incontinence, colostomies, and similar procedures, as well as body odor in general. It is also available as a topical preparation, purportedly useful for both treatment and odor control of wounds, injuries, radiation burns, and other skin conditions."Chlorophyllin Uses, Side Effects & Warnings". Drugs.com. Retrieved 2020-03-29. Chlorophyllin has been used in alternative medicine as an aid to reduce the odor of urine or feces (bowel movements).

3D printing

Chlorophyllin has been used as a biocompatible photoblocker for generating green colored hydrogels with complex inner structures.^[2]

Chemical properties

Chlorophyllin is water-soluble. In vitro, it binds to some environmental mutagens such as the polycyclic aromatic hydrocarbons benzo[a]pyrene^[3] and dibenzo[a,i]pyrene.^[4] Chlorophyllin also binds to acridine orange.^[5]

References

^ "Duranat Cu Chlorophyllin WSP (Natural Green 3-1 CI 75810-1)". Retrieved 15 October 2012.
^ Benjamin, Aaron D.; Abbasi, Reha; Owens, Madison; Olsen, Robert J.; Walsh, Danica J.; Lefevre, Thomas B.; Wilking, James N. (2019). "Light-based 3D printing of hydrogels with high-resolution channels". Biomedical Physics & Engineering Express. 5 (2): 025035. doi:10.1088/2057-1976/aad667.
^ Keshava C, Divi RL, Einem TL, Richardson DL, Leonard SL, Keshava N, Poirier MC, Weston A (2009). "Chlorophyllin significantly reduces benzo[a]pyrene-DNA adduct formation and alters cytochrome P450 1A1 and 1B1 expression and EROD activity in normal human mammary epithelial cells". Environmental and Molecular Mutagenesis. 50 (2): 134–144. doi:10.1002/em.20449. PMC 2637934. PMID 19152381.
^ Castro DJ, Löhr CV, Fischer KA, Waters KM, Webb-Robertson BJ, Dashwood RH, Bailey GS, Williams DE (2009). "Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesi". Carcinogenesis. 30 (2): 315–320. doi:10.1093/carcin/bgn280. PMC 2722150. PMID 19073876.
^ Osowski A, Pietrzak M, Wieczorek Z, Wieczorek J (2010). "Natural compounds in the human diet and their ability to bind mutagens prevents DNA-mutagen intercalation". Journal of Toxicology and Environmental Health, Part A. 73 (17–18): 1141–1149. doi:10.1080/15287394.2010.491044. PMID 20706936.

External links

Chlorophyll and Chlorophyllin, Linus Pauling Institute, Oregon State University
2002 Video from CNN
Food-Info.net

[1] "Duranat Cu Chlorophyllin WSP (Natural Green 3-1 CI 75810-1)". Retrieved 15 October 2012.

[2] Benjamin, Aaron D.; Abbasi, Reha; Owens, Madison; Olsen, Robert J.; Walsh, Danica J.; Lefevre, Thomas B.; Wilking, James N. (2019). "Light-based 3D printing of hydrogels with high-resolution channels". Biomedical Physics & Engineering Express. 5 (2): 025035. doi:10.1088/2057-1976/aad667.

[3] Keshava C, Divi RL, Einem TL, Richardson DL, Leonard SL, Keshava N, Poirier MC, Weston A (2009). "Chlorophyllin significantly reduces benzo[a]pyrene-DNA adduct formation and alters cytochrome P450 1A1 and 1B1 expression and EROD activity in normal human mammary epithelial cells". Environmental and Molecular Mutagenesis. 50 (2): 134–144. doi:10.1002/em.20449. PMC 2637934. PMID 19152381.

[DJCastro-4] Castro DJ, Löhr CV, Fischer KA, Waters KM, Webb-Robertson BJ, Dashwood RH, Bailey GS, Williams DE (2009). "Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesi". Carcinogenesis. 30 (2): 315–320. doi:10.1093/carcin/bgn280. PMC 2722150. PMID 19073876.

[5] Osowski A, Pietrzak M, Wieczorek Z, Wieczorek J (2010). "Natural compounds in the human diet and their ability to bind mutagens prevents DNA-mutagen intercalation". Journal of Toxicology and Environmental Health, Part A. 73 (17–18): 1141–1149. doi:10.1080/15287394.2010.491044. PMID 20706936.

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