Chlorophyllin

Chlorophyllin is a semi-synthetic, water-soluble derivative of chlorophyll, the green pigment found in plants. It is typically produced from chlorophyll through a process involving saponification (removal of the phytol tail) and the replacement of the central magnesium atom with copper. These modifications enhance its stability, deep green color, and water solubility compared to natural chlorophyll. Chlorophyllin is widely used as a food coloring and is a common ingredient in dietary supplements.

Chemical Structure and Properties

Chlorophyllin differs from natural chlorophyll in several key ways:

Water Solubility: The long, hydrophobic phytol tail present in chlorophyll is removed during saponification, replaced by various small, polar groups (such as carboxylic acid groups or their salts). This structural change makes chlorophyllin highly water-soluble.
Metal Ion: The central magnesium ion of natural chlorophyll is typically replaced by copper, forming copper chlorophyllin (CI 75815), which contributes to its enhanced stability against light and acid, and its distinct dark green hue. Sodium, potassium, and iron salts of chlorophyllin are also known.
Appearance: Chlorophyllin typically presents as a dark green to black powder.
Stability: It exhibits greater stability to light, heat, and acidic conditions compared to chlorophyll.

Production

Chlorophyllin is primarily derived from chlorophyll extracted from green plants such as alfalfa, nettle, spinach, grass, or the microalga spirulina. The production process generally involves two main steps:

Saponification: Chlorophyll is treated with an alkali (e.g., sodium hydroxide or potassium hydroxide) to hydrolyze the phytol ester, producing chlorophyllides, which are water-soluble.
Metal Chelation: The magnesium atom in the chlorophyllide molecule is then replaced by copper (or sometimes iron) through chelation with a copper salt (e.g., copper sulfate). The resulting product is usually purified and sold as a sodium and/or potassium salt of copper chlorophyllin.

Uses

Food Additive

Chlorophyllin and its copper complexes are widely employed as food colorings due to their vibrant green color and stability.

E-numbers: In Europe, sodium copper chlorophyllin is designated as E141 (while chlorophyll is E140).
Applications: It is used to color a broad range of food products, including confectionery, ice cream, pasta, chewing gum, beverages, sauces, dairy products, and certain baked goods.

Dietary Supplement

Chlorophyllin is a popular ingredient in dietary supplements, often marketed for various health benefits:

Internal Deodorant: It is traditionally used as an internal deodorant, believed to neutralize body odors, bad breath, and odors associated with conditions like colostomies or ileostomies.
Antioxidant Properties: Research suggests that chlorophyllin possesses antioxidant activity, helping to protect cells from oxidative damage caused by free radicals.
Anticarcinogenic Potential: Some studies indicate that chlorophyllin may help prevent certain types of cancer by forming complexes with potential carcinogens (e.g., aflatoxins, heterocyclic amines) and inhibiting their absorption, thereby reducing their bioavailability and subsequent damage to DNA.
Wound Healing: It has been historically incorporated into some topical preparations for promoting wound healing and reducing inflammation.

Other Applications

Cosmetics: Used in some cosmetic products for its coloring and potential deodorizing properties.
Pharmaceuticals: Investigated for use in certain medical applications, particularly those related to detoxification and oxidative stress.

Safety and Regulation

Chlorophyllin is generally recognized as safe (GRAS) by regulatory bodies worldwide.

United States: The U.S. Food and Drug Administration (FDA) approves its use as a color additive in certain foods and as a dietary supplement.
European Union: The European Food Safety Authority (EFSA) permits it as a food additive (E141).
Side Effects: While generally safe, high doses may cause temporary discoloration of urine or feces (greenish tint), or mild gastrointestinal upset in some individuals.

References

Ames, B. N., Shigenaga, M. K., & Hagen, T. M. (1995). Oxidants, antioxidants, and the degenerative diseases of aging. Proceedings of the National Academy of Sciences, 92(3), 2365-2372.
Egner, P. A., et al. (2001). Chlorophyllin intervention reduces aflatoxin-DNA adducts in individuals at high risk for liver cancer. Proceedings of the National Academy of Sciences, 98(25), 14601-14606.
European Food Safety Authority (EFSA) opinions on food additives E140 and E141.
U.S. Food and Drug Administration (FDA) regulations on color additives and dietary supplements.

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