Chlorophyllin

Chlorophyllin
Structural formula of chlorophyllin, sodium salt
Space-filling model of the chlorophyllin molecule, sodium salt
Names
Other names
Natural green 3, E141
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.031.117 Edit this at Wikidata
UNII
  • 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 checkY
    Key: OYINILBBZAQBEV-HHGNVTQFSA-N checkY
  • 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
  • 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
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).

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. Also in recent years it has been used as a home remedy to treat acne and skin conditions such as pimples or blackheads, thanks to its antimicrobial effect. 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.[2] The origins of these unsubstantiated medical claims were findings from research by F. Howard Westcott in the 1940s that it was an odor blocker. The commercial value of this attribute in advertising led to many companies creating brands containing the compound in 1950–1953 in particular. It was used as a marketing tool to promote toothpaste, sanitary towels, soap and other products. However, it was soon determined that the hype surrounding chlorophyll or chlorophyllin was not warranted and the underlying research may even have been a hoax. As a result, brands rapidly discontinued its use. In the 2020s, it again became the subject of unsubstantiated medical claims, as social media influencers promoted its use in the form of "chlorophyll water", for example.[3]

3D printing

Chlorophyllin has been used as a biocompatible photoblocker for generating green colored hydrogels with complex inner structures.[4]

Chemical properties

Chlorophyllin is water-soluble. In vitro, it binds to some environmental mutagens such as the polycyclic aromatic hydrocarbons benzo[a]pyrene[5] and dibenzo[a,i]pyrene.[6] Chlorophyllin also binds to acridine orange.[7]

Biological properties

Chlorophyllin has been validated to exhibit ameliorative effects against food additive induced genotoxicity (elevating the expression of DNA repair proteins p53 and PARP) and mitochondrial dysfunction and may be used as a therapeutic tool for the management of diseases like diabetes and cancer.[8][9] It has shown to modulate several protein functions including the expression of cytokine proteins NFkβ and IFNγ.[10]

References

  1. ^ "Duranat Cu Chlorophyllin WSP (Natural Green 3-1 CI 75810-1)". Retrieved 15 October 2012.
  2. ^ "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).
  3. ^ O'Hagan LA (2022). "All that glistens is not (Green) gold: Historicising the contemporary chlorophyll fad through a multimodal analysis of Swedish marketing, 1950–1953". Journal of Historical Research in Marketing. 14 (3): 374–398. doi:10.1108/jhrm-11-2021-0057.
  4. ^ Benjamin AD, Abbasi R, Owens M, Olsen RJ, Walsh DJ, Lefevre TB, Wilking JN (2019). "Light-based 3D printing of hydrogels with high-resolution channels". Biomedical Physics & Engineering Express. 5 (2): 025035. doi:10.1088/2057-1976/aad667.
  5. ^ 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. Bibcode:2009EnvMM..50..134K. doi:10.1002/em.20449. PMC 2637934. PMID 19152381.
  6. ^ 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.
  7. ^ 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. Bibcode:2010JTEHA..73.1141O. doi:10.1080/15287394.2010.491044. PMID 20706936. S2CID 11060470.
  8. ^ Asmita S, Sudatta D, Priyanka S, Ruchira D, Sisir N, Jayeeta D, Banani B, Arnob C, Maharaj B, Pradeepta G (2021-10-31). "Phyto-chlorophyllin Prevents Food Additive Induced Genotoxicity and Mitochondrial Dysfunction via Cytochrome c Mediated Pathway in Mice Model". Combinatorial Chemistry & High Throughput Screening. 24 (10): 1618–1627. doi:10.2174/1386207323666201230093510. PMID 33380297. S2CID 229929638.
  9. ^ Das J, Samadder A, Mondal J, Abraham SK, Khuda-Bukhsh AR (2016-09-01). "Nano-encapsulated chlorophyllin significantly delays progression of lung cancer both in in vitro and in vivo models through activation of mitochondrial signaling cascades and drug-DNA interaction". Environmental Toxicology and Pharmacology. 46: 147–157. Bibcode:2016EnvTP..46..147D. doi:10.1016/j.etap.2016.07.006. ISSN 1382-6689. PMID 27458703.
  10. ^ Samadder A, Das S, Pal B, Das S, Mandal A, Biswas P, Ghosh S, Mandal SH, Sow P, Das R, Biswas S, Panigrahi AK (November 24, 2021). "First report on chlorophyllin to protect mammalian and fish muscle cells from pesticide toxicity via activation of p53 and PARP". Aquaculture and Fisheries. 6 (4): 393–399. Bibcode:2021AqFis...6..393S. doi:10.1016/j.aaf.2020.07.008. S2CID 225189893.