Chlorophyllin

Chlorophyllin

Space-filling model of the chlorophyllin molecule, sodium salt
Names
Other names Natural green 3, E141
Identifiers
CAS Number	11006-34-1 Y
ChemSpider	4586363 Y
Jmol 3D model	Interactive image Interactive image
PubChem	5479494
UNII	1D276TYV9O Y
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 Y Key: OYINILBBZAQBEV-HHGNVTQFSA-N Y 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 C=CC3=C(C)C4=CC(C(C)C8CCC([O-])=O)=[N@]2C8=C(CC([O-])=O)C1=C(C([O-])=O)C(C)=C7N1[Cu@]52[N@@]6=C(C(C)=C(CC)C6=C7)C=C3N45.[Na+].[Na+].[Na+] O=C(O)CC[C@@H]5c3nc(cc4c(c(\C=C)c(cc1c(c(c(n1)cc\2nc(/C(=C/2C)C(=O)O)c3CC(=O)O)CC)C)n4)C)[C@H]5C
Properties
Chemical formula	C34H31CuN4Na3O6
Molar mass	724.15 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. Chlorophyll is present in green leafy vegetables and reaching levels as high as 5.7% in spinach. As a food coloring agent, copper complex chlorophyllin is known as natural green 3 and has the E number E141.

Uses

Cancer prevention

Because chlorophyll does not dissolve in water, food sources of chlorophyll do not bind to mutagenic substances to a significant extent. Chlorophyllin, being water-soluble, can significantly bind to environmental mutagens such as the polycyclic aromatic hydrocarbons benzo[a]pyrene and dibenzo{a,i}pyrene. Chlorophyllin binds to mutagens twenty times better than resveratrol and thousands of times better than xanthines.

Medicine and hygiene

Chlorophyllin is the active ingredient in a number of internally taken preparations 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, and other skin conditions—notably radiation burns.

Chemistry

PEG-Chlorophyllin is conjugated with the following

α-(3-aminopropyl)-ω-methoxypoly(oxyethylene), PEG-NH2, to form the PEG−chlorophyllin conjugate through acid-amide bonds. PEG−chlorophyllin conjugate was stable toward light illumination under anaerobic condition in comparison with chlorophyllin a. The conjugate catalyzed the reduction of methyl viologen in the presence of 2-mercaptoethanol and the evolution of hydrogen gas in the presence of methyl viologen (an electron carrier), 2-mercaptoethanol (an electron donor) and hydrogenase (Scheme 1). Furthermore, the PEG−chlorophyllin conjugate catalyzed the photoreduction of NADP+ or NAD+ in the presence of ascorbate as an electron donor and ferredoxin-NADP+ reductase as the coupling enzyme. Utilizing the reducing power of NADPH generated by the PEG−chlorophyllin conjugate under the illumination, CO₂ fixation was accomplished by the synthesis of malate (C4) from pyruvate (C3) and CO₂ in the presence of malic enzyme (Scheme 2). These reactions mentioned above can not proceed in the dark or without each enzyme.

External links

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