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Anthocyanins may protect the leaves from attacks by herbivores that may be attracted by green color.
Anthocyanins are found in the cell vacuole, mostly in flowers and fruits, but also in leaves, stems, and roots.
Anthocyanins occur in the flowers of many plants, such as the blue poppies of some Meconopsis species and cultivars.
CAS Number: 11029-12-2
Molecular Formula: C15H11O+
Molecular Weight: 207.24724
Synonyms: GRAPE SKIN EXTRACT 30% POLYPHENOLS, Anthocyanins, grape, BLUEBERRYANTHOCYANINS, GRAPEJUICECOLOUR, HIBISCUSSABDARIFFAL.ANTHOCYANINS, GRAPESKINCOLOUR, PURPLECORNCOLOUR, TAMARINDCOLOUR, ANTHOCYANIDINS, 10% BY UV FROM BILBERRY P.E., 11029-12-2, GRAPE SKIN EXTRACT 30% POLYPHENOLS
Anthocyanins 'flower' and κυάνεος/κυανοῦς (kuáneos/kuanoûs) 'dark blue'), also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black.
In 1835, the German pharmacist Ludwig Clamor Marquart named a chemical compound that gives flowers a blue color, Anthokyan, in his treatise "Die Farben der Blüthen" (English: The Colors of Flowers).
Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black.
Some of the colors of autumn leaves are derived from anthocyanins.
Anthocyanins belong to a parent class of molecules called flavonoids synthesized via the phenylpropanoid pathway.
They can occur in all tissues of higher plants, including leaves, stems, roots, flowers, and fruits.
Anthocyanins are derived from anthocyanidins by adding sugars.
They are odorless and moderately astringent.
Although approved as food and beverage colorant in the European Union, anthocyanins are not approved for use as a food additive because they have not been verified as safe when used as food or supplement ingredients.
There is no conclusive evidence that anthocyanins have any effect on human biology or diseases.
Anthocyanins are a group of naturally occurring water-soluble pigments belonging to the larger family of flavonoids, which are widely distributed in the plant kingdom and responsible for the vivid red, purple, and blue colors found in many fruits, vegetables, flowers, and leaves.
Chemically, anthocyanins are glycosides of anthocyanidins, meaning that they consist of an anthocyanidin molecule bonded to one or more sugar molecules, which greatly influences their solubility, stability, and color expression depending on the pH and environmental conditions.
These pigments play a crucial role in plants not only by imparting attractive colors that help in the attraction of pollinators and seed dispersers, such as bees, birds, and mammals, but also by providing protection against various types of environmental stress, including ultraviolet radiation, temperature extremes, and pathogen attacks.
In particular, anthocyanins function as antioxidants, scavenging harmful free radicals and reactive oxygen species that can damage plant cells, thereby contributing to the plant’s overall health and resilience.
The absorbance pattern responsible for the red color of anthocyanins may be complementary to that of green chlorophyll in photosynthetically active tissues such as young Quercus coccifera leaves.
In these parts, they are found predominantly in outer cell layers such as the epidermis and peripheral mesophyll cells.
Most frequently occurring in nature are the glycosides of cyanidin, delphinidin, malvidin, pelargonidin, peonidin, and petunidin.
Roughly 2% of all hydrocarbons fixed in photosynthesis are converted into flavonoids and their derivatives, such as the anthocyanins.
Not all land plants contain anthocyanin; in the Caryophyllales (including cactus, beets, and amaranth), they are replaced by betalains.
Anthocyanins and betalains have never been found in the same plant.
Sometimes bred purposely for high anthocyanin content, ornamental plants such as sweet peppers may have unusual culinary and aesthetic appeal.
Anthocyanins have also been found in various tulip flowers, such as Tulipa gesneriana, Tulipa fosteriana and Tulipa eichleri.
Plants rich in anthocyanins are Vaccinium species, such as blueberry, cranberry, and bilberry; Rubus berries, including black raspberry, red raspberry, and blackberry; blackcurrant, cherry, eggplant (aubergine) peel, black rice, ube, Okinawan sweet potato, Concord grape, muscadine grape, red cabbage, and violet petals.
Red-fleshed peaches and apples contain anthocyanins.
Anthocyaninss are less abundant in banana, asparagus, pea, fennel, pear, and potato, and may be totally absent in certain cultivars of green gooseberries.
The highest recorded amount appears to be specifically in the seed coat of black soybean containing approximately 2 g per 100 g, in purple corn kernels and husks, and in the skins and pulp of black chokeberry.
Due to critical differences in sample origin, preparation, and extraction methods determining anthocyanin content, the values presented in the adjoining table are not directly comparable.
Nature, traditional agriculture methods, and plant breeding have produced various uncommon crops containing anthocyanins, including blue- or red-flesh potatoes and purple or red broccoli, cabbage, cauliflower, carrots, and corn.
Garden tomatoes have been subjected to a breeding program using introgression lines of genetically modified organisms (but not incorporating them in the final purple tomato) to define the genetic basis of purple coloration in wild species that originally were from Chile and the Galapagos Islands.
The variety known as "Indigo Rose" became available commercially to the agricultural industry and home gardeners in 2012.
Investing tomatoes with high anthocyanin content doubles their shelf-life and inhibits growth of a post-harvest mold pathogen, Botrytis cinerea.
Some tomatoes also have been modified genetically with transcription factors from snapdragons to produce high levels of anthocyanins in the fruits.
Anthocyanins also may be found in naturally ripened olives, and are partly responsible for the red and purple colors of some olives.
In terms of human health and nutrition, anthocyanins have attracted significant scientific interest due to their potential antioxidant, anti-inflammatory, and anti-carcinogenic properties, which may help reduce the risk of chronic diseases such as cardiovascular disease, certain cancers, and neurodegenerative disorders.
These compounds are abundant in commonly consumed foods like berries (blueberries, raspberries, blackberries), grapes, red cabbage, eggplants, and purple sweet potatoes, making them important contributors to the dietary intake of bioactive phytochemicals.
The color and stability of anthocyanins are highly sensitive to pH changes: in acidic environments, they typically appear red, whereas in neutral to alkaline conditions, their color shifts to purple or blue, which is why they are also used as natural pH indicators in some applications.
Because of their natural origin and vibrant coloration, anthocyanins are widely explored as natural food colorants and additives, offering an alternative to synthetic dyes in the food, cosmetic, and pharmaceutical industries.
storage temp.: -20 °C
solubility: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
form: Solid
color: Very Dark Purple to Black
Odor: odorless
Odor Type: odorless
InChI: InChI=1S/C15H11O/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H/q+1
InChIKey: NWKFECICNXDNOQ-UHFFFAOYSA-N
Anthocyanins fluoresce, enabling a tool for plant cell research to allow live cell imaging without a requirement for other fluorophores.
Anthocyanin production may be engineered into genetically modified materials to enable their identification visually.
Anthocyanins are approved for use as food colorants in the European Union, Australia, and New Zealand, having colorant code E163.
In 2013, a panel of scientific experts for the European Food Safety Authority concluded that anthocyanins from various fruits and vegetables have been insufficiently characterized by safety and toxicology studies to approve their use as food additives.
Extending from a safe history of using red grape skin extract and blackcurrant extracts to color foods produced in Europe, the panel concluded that these extract sources were exceptions to the ruling and were sufficiently shown to be safe.
Anthocyanin extracts are not specifically listed among approved color additives for foods in the United States; however, grape juice, red grape skin and many fruit and vegetable juices, which are approved for use as colorants, are rich in naturally occurring anthocyanins.
No anthocyanin sources are included among approved colorants for drugs or cosmetics.
When esterified with fatty acids, anthocyanins can be used as a lipophilic colorant for foods.
The reds, purples, and their blended combinations responsible for autumn foliage are derived from anthocyanins.
Unlike carotenoids, anthocyanins are not present in the leaf throughout the growing season, but are produced actively, toward the end of summer.
They develop in late summer in the sap of leaf cells, resulting from complex interactions of factors inside and outside the plant.
Their formation depends on the breakdown of sugars in the presence of light as the level of phosphate in the leaf is reduced.
Orange leaves in autumn result from a combination of anthocyanins and carotenoids.
Anthocyanins are present in approximately 10% of tree species in temperate regions, although in certain areas such as New England, up to 70% of tree species may produce anthocyanins.
The anthocyanins, anthocyanidins with sugar group(s), are mostly 3-glucosides of the anthocyanidins.
The anthocyanins are subdivided into the sugar-free anthocyanidin aglycones and the anthocyanin glycosides.
As of 2003, more than 400 anthocyanins had been reported, while later literature in early 2006, puts the number at more than 550 different anthocyanins.
The difference in chemical structure that occurs in response to changes in pH, is the reason why anthocyanins often are used as pH indicators, as they change from red in acids to blue in bases through a process called halochromism.
Red to dark purple liquid, lump, powder or paste, with a slight odor. Soluble in water, ethanol, propylene glycol, insoluble in oil.
Flavylium is a member of the class of chromenyliums that is chromenylium with a phenyl substituent at position 2.
Anthocyanins is functionally related to a chromenylium.
Content of anthocyanins in the leaves of colorful plant foods such as purple corn, blueberries, or lingonberries, is about ten times higher than in the edible kernels or fruit.
The color spectrum of grape berry leaves may be analysed to evaluate the amount of anthocyanins.
Fruit maturity, quality, and harvest time may be evaluated on the basis of the spectrum analysis.
Anthocyanins are thought to be subject to physiochemical degradation in vivo and in vitro.
Structure, pH, temperature, light, oxygen, metal ions, intramolecular association, and intermolecular association with other compounds (copigments, sugars, proteins, degradation products, etc.) generally are known to affect the color and stability of anthocyanins.
B-ring hydroxylation status and pH have been shown to mediate the degradation of anthocyanins to their phenolic acid and aldehyde constituents.
Indeed, significant portions of ingested anthocyanins are likely to degrade to phenolic acids and aldehyde in vivo, following consumption.
This characteristic confounds scientific isolation of specific anthocyanin mechanisms in vivo.
Enocyanin was producted by refining and vacuum concentration of the peel (residue after making grape juice or wine) of Vitis vinifera.
Anthocyanins have been used in organic solar cells because of their ability to convert light energy into electrical energy.
The many benefits to using dye-sensitized solar cells instead of traditional p-n junction silicon cells, include lower purity requirements and abundance of component materials, as well as the fact that they may be produced on flexible substrates, making them amenable to roll-to-roll printing processes.
Anthocyanins are somewhat unstable and susceptible to degradation by factors such as heat, light, oxygen, and enzymes, which can limit their use and effectiveness in processed products.
To overcome these challenges, various stabilization techniques such as microencapsulation, copigmentation, and complexation with metals or other molecules are researched and applied to preserve their color and bioactivity during storage and processing.
Enocyanin is an Anthocyanins obtained from grapes.
Anthocyanins can affect the activities of leucine aminopeptidase, acid phosphatase, γ-glutamyl transpeptidase and esterase.
In flowers, the coloration that is provided by anthocyanin accumulation may attract a wide variety of animal pollinators, while in fruits, the same coloration may aid in seed dispersal by attracting herbivorous animals to the potentially-edible fruits bearing these red, blue, or purple colors.
Anthocyanins may have a protective role in plants against extreme temperatures.
Tomato plants protect against cold stress with anthocyanins countering reactive oxygen species, leading to a lower rate of cell death in leaves.
Uses:
Anthocyanins can be used as colorant (red to magenta) for beverages, cold drinks, alcoholic beverages, cakes, jams, etc.
anthocyanins are employed in agriculture and horticulture to breed plants and crops with enhanced aesthetic appeal and improved stress resistance.
By understanding and manipulating anthocyanin biosynthesis pathways, breeders can produce fruits, flowers, and vegetables with intensified colors that attract pollinators or consumers, while also potentially increasing the plants’ tolerance to UV radiation and pathogens.
Anthocyanins are widely utilized in various industries and applications due to their vibrant colors, antioxidant properties, and natural origin, making them highly valued both as functional ingredients and as natural colorants.
One of the primary uses of anthocyanins is in the food industry, where they serve as natural coloring agents that impart attractive red, purple, or blue hues to products such as beverages, jams, jellies, confectionery, yogurts, and baked goods.
Because consumer demand for clean-label and naturally derived ingredients has increased significantly in recent years, anthocyanins provide a desirable alternative to synthetic dyes, allowing manufacturers to enhance the visual appeal of food products while catering to health-conscious and environmentally aware customers.
In addition to their coloring function, anthocyanins are prized for their antioxidant activity, which is harnessed in the development of functional foods and dietary supplements aimed at promoting health and preventing disease.
Their ability to neutralize free radicals contributes to reducing oxidative stress in the body, which is linked to aging and various chronic conditions, including cardiovascular diseases, cancer, and neurodegenerative disorders.
As a result, anthocyanin-rich extracts from berries, grapes, and other sources are incorporated into nutraceutical products designed to support heart health, improve cognitive function, and enhance overall wellbeing.
The cosmetic industry also makes use of anthocyanins due to their antioxidant and anti-inflammatory properties, incorporating them into formulations for skin care products such as creams, serums, and lotions that aim to protect the skin from environmental damage and reduce signs of aging.
Their natural pigment provides gentle coloring effects in lipsticks, blushes, and hair dyes, appealing to consumers who prefer botanical and toxin-free ingredients in their beauty routines.
Furthermore, anthocyanins find applications in the pharmaceutical sector, where their bioactive properties are explored for the development of therapies that target inflammation, oxidative damage, and microbial infections.
Research into their potential roles in managing metabolic syndrome, diabetes, and certain types of cancers continues to expand, positioning anthocyanins as promising compounds in complementary and alternative medicine.
In scientific research and education, anthocyanins are used as natural pH indicators because their color changes distinctly in response to different pH levels—ranging from red in acidic solutions to purple or blue in alkaline environments—making them useful in chemical demonstrations and analytical assays.
Anthocyanins are extensively valued not only for their natural pigmentation but also for their remarkable functional and health-promoting properties, which have driven their increasing incorporation into a wide array of products across multiple industries worldwide.
In the realm of the food and beverage industry, these pigments are commonly extracted from natural sources such as blueberries, blackberries, elderberries, and red cabbage, and subsequently used to enhance the color profile of fruit juices, soft drinks, wines, and flavored waters, thereby improving consumer appeal through visually striking hues that range from deep reds to purples and blues.
Importantly, the use of anthocyanins as natural colorants aligns perfectly with the modern trend toward clean-label products—foods formulated without synthetic additives—which is increasingly favored by health-conscious consumers seeking transparency and safety in their food choices.
Beyond simply coloring food products, anthocyanins are often marketed as bioactive compounds in the development of functional foods and dietary supplements, where they contribute antioxidant and anti-inflammatory effects that are believed to support cardiovascular health, improve visual acuity, and even promote cognitive function.
These applications rely on the fact that anthocyanins help neutralize harmful free radicals and reduce oxidative damage at the cellular level, which is implicated in the aging process and the onset of chronic illnesses.
As a result, extracts standardized for high anthocyanin content are incorporated into capsules, powders, and fortified food products, targeting consumers interested in natural health promotion and disease prevention.
In scientific and educational contexts, anthocyanins serve as useful natural pH indicators because their color shifts dramatically depending on the acidity or alkalinity of the environment, making them excellent tools for chemistry demonstrations and qualitative analysis without the use of synthetic dyes.
This property also finds practical application in intelligent packaging systems, where anthocyanin-based materials can signal food spoilage or changes in freshness by changing color, thereby improving food safety and reducing waste.
Moreover, in plant breeding and agriculture, anthocyanins are not only important for creating visually appealing fruits and flowers but also for enhancing plants’ ability to cope with abiotic stresses such as UV radiation, drought, and extreme temperatures.
Breeders and genetic engineers often target the pathways involved in anthocyanin biosynthesis to develop crop varieties that are more resilient to climate challenges while offering increased nutritional value and improved aesthetic qualities that attract consumers and pollinators alike.
Safety Profile:
Anthocyanins, being natural plant pigments commonly found in fruits and vegetables, are generally considered safe for human consumption and are widely recognized for their beneficial health effects; however, when concentrated in extracts or used in industrial applications, certain hazards and considerations must be taken into account.
Firstly, although anthocyanins themselves are not typically toxic, some commercial extracts may contain impurities or residual solvents from the extraction process, which can pose risks if not properly purified or handled.
These impurities could potentially cause allergic reactions, skin irritation, or respiratory sensitization in sensitive individuals, especially when handled as powders or concentrated solutions in occupational settings.
From a chemical stability perspective, anthocyanins are known to be quite unstable and susceptible to degradation when exposed to factors such as heat, light, oxygen, and pH extremes.
During manufacturing or storage, their breakdown products might include compounds whose safety profiles are less well understood, so careful control of processing conditions is necessary to minimize the formation of potentially harmful substances.
Additionally, because anthocyanin extracts often contain other bioactive flavonoids or phytochemicals, there is a slight possibility of interactions with medications or allergic reactions in rare cases, particularly when consumed in high doses through supplements.
In terms of environmental hazards, anthocyanins themselves are biodegradable and pose little risk to ecosystems; however, the solvents and chemicals used for their extraction and processing—such as ethanol, methanol, or acids—can present flammability, toxicity, or environmental contamination hazards if not managed properly.
Therefore, industrial facilities that produce or handle anthocyanin extracts must adhere to strict safety and environmental regulations to prevent accidental releases and exposure.
