E160d (Lycopene)

EC / List no.: 207-949-1
CAS no.: 502-65-8
Mol. formula: C40H56

E160d (Lycopene) (from the neo-Latin Lycopersicum, the tomato species) is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables, such as red carrots, watermelons, grapefruits, and papayas. 
E160d (Lycopene) is not present in strawberries or cherries.
Although lycopene is chemically a carotene, it has no vitamin A activity.

In plants, algae, and other photosynthetic organisms, lycopene is an intermediate in the biosynthesis of many carotenoids, including beta-carotene, which is responsible for yellow, orange, or red pigmentation, photosynthesis, and photoprotection.
Like all carotenoids, lycopene is a tetraterpene.
E160d (Lycopene) is insoluble in water. Eleven conjugated double bonds give lycopene its deep red color. 
Owing to the strong color, lycopene is useful as a food coloring (registered as E160d) and is approved for use in the USA, Australia and New Zealand (registered as 160d) and the European Union.

Structure and physical properties
E160d (Lycopene) is a symmetrical tetraterpene, i.e. assembled from eight isoprene units. 
E160d (Lycopene) is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also classified as a carotene.
Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. 
In its natural, all-trans form, the molecule is long and straight, constrained by its system of 11 conjugated double bonds. 
Each extension in this conjugated system reduces the energy required for electrons to transition to higher energy states, allowing the molecule to absorb visible light of progressively longer wavelengths. E160d (Lycopene) absorbs all but the longest wavelengths of visible light, so it appears red.

Plants and photosynthetic bacteria naturally produce all-trans lycopene.
When exposed to light or heat, lycopene can undergo isomerization to any of a number of cis-isomers, which have a bent rather than linear shape. 
Different isomers were shown to have different stabilities due to their molecular energy (highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest).
In human blood, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.

Carotenoids like lycopene are found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae.
They are responsible for the bright orange–red colors of fruits and vegetables, perform various functions in photosynthesis, and protect photosynthetic organisms from excessive light damage. 
E160d (Lycopene) is a key intermediate in the biosynthesis of carotenoids, such as beta-carotene, and xanthophylls.

Dispersed lycopene molecules can be encapsulated into carbon nanotubes enhancing their optical properties.
Efficient energy transfer occurs between the encapsulated dye and nanotube — light is absorbed by the dye and without significant loss is transferred to the nanotube. 
Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization.

Biosynthesis
The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.
Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. 
This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon geranylgeranyl pyrophosphate. 
Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon phytoene, the first committed step in carotenoid biosynthesis. 
Through several desaturation steps, phytoene is converted into lycopene. 
The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls.

Staining and removal
E160d (Lycopene) is the pigment in tomato sauces that turns plastic cookware orange. 
E160d (Lycopene) is insoluble in plain water, but it can be dissolved in organic solvents and oils. 
Because of its non-polarity, lycopene in food preparations will stain any sufficiently porous material, including most plastics. 
To remove this staining, the plastics may be soaked in a solution containing a small amount of chlorine bleach.
The bleach oxidizes the lycopene, thus allowing the now-polarized product to dissolve.

Diet
Consumption by humans
Absorption of lycopene requires that it be combined with bile salts and fat to form micelles.
Intestinal absorption of lycopene is enhanced by the presence of fat and by cooking.
E160d (Lycopene) dietary supplements (in oil) may be more efficiently absorbed than lycopene from food.

E160d (Lycopene) is not an essential nutrient for humans, but is commonly found in the diet mainly from dishes prepared from tomatoes.
The median and 99th percentile of dietary lycopene intake have been estimated to be 5.2 and 123 mg/d, respectively.

Sources
Fruits and vegetables that are high in lycopene include autumn olive, gac, tomatoes, watermelon, pink grapefruit, pink guava, papaya, seabuckthorn, wolfberry (goji, a berry relative of tomato), and rosehip.
Ketchup is a common dietary source of lycopene.
Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes), tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.
The lycopene content of tomatoes depends on variety and increases as the fruit ripens.

Unlike other fruits and vegetables, where nutritional content such as vitamin C is diminished upon cooking, processing of tomatoes increases the concentration of bioavailable lycopene.
E160d (Lycopene) in tomato paste is up to four times more bioavailable than in fresh tomatoes.
Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes.

Cooking and crushing tomatoes (as in the canning process) and serving in oil-rich dishes (such as spaghetti sauce or pizza) greatly increases assimilation from the digestive tract into the bloodstream. E160d (Lycopene) is fat-soluble, so the oil is said to help absorption. 
Gac has high lycopene content derived mainly from its seed coats.
Cara cara navel, and other citrus fruit, such as pink grapefruit, also contain lycopene.
Some foods that do not appear red also contain lycopene, e.g., asparagus, which contains about 30 μg of lycopene per 100-g serving (0.3 μg/g) and dried parsley and basil, which contain around 3.5–7.0 μg/g of lycopene.
When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes.

Adverse effects
E160d (Lycopene) is non-toxic and commonly found in the diet, mainly from tomato products. 
There are cases of intolerance or allergic reaction to dietary lycopene, which may cause diarrhea, nausea, stomach pain or cramps, gas, and loss of appetite.
E160d (Lycopene) may increase the risk of bleeding when taken with anticoagulant drugs.
Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. 
E160d (Lycopene) may affect the immune system, the nervous system, sensitivity to sunlight, or drugs used for stomach ailments.

E160d (Lycopene)mia is an orange discoloration of the skin that is observed with high intakes of lycopene.
The discoloration is expected to fade after discontinuing excessive lycopene intake

Description    
E160d (Lycopene) is a red-colored carotenoid found in tomatoes and other red fruits and vegetables. 
Carotenoids, including lycopene, are powerful antioxidants that efficiently quench singlet oxygen. 
Presumably through this action, carotenoids may protect against cancers, cardiovascular stress, and other diseases.

Chemical Properties    
E160d (Lycopene) is a white to pale-yellow solid; balsam oriental aroma. 
E160d (Lycopene) extract from tomato is a dark-red viscous liquid. 
E160d (Lycopene) is freely soluble in ethyl acetate and n-hexane, partially soluble in ethanol and acetone, and insoluble in water. 
A solution in n-hexane shows an absorption maximum at approximately 472nm.
E160d (Lycopene) (from the Greek word lykopersikon, meaning tomato) is a bright red carotene and carotenoid pigment. 
The natural resources are red fruits and vegetables, such as tomatoes, pink grapefruit, watermelon, and apricots. 
After absorbing from the stomach, lycopene is transported in the blood and accumulates in the liver, adrenal glands, and testes. 
E160d (Lycopene) has been used to prevent carcinogenesis, cardiovascular diseases and aging.
From a chemistry perspective, lycopene is a symmetrical tetraterpene assembled from 8 isoprene units, containing 11 conjugated and 2 non-conjugated double bonds between carbon atoms. 
E160d (Lycopene) is a member of the carotenoid family, and the predominant source in the human diet comes from tomato and tomato-based products. 
The antioxidant capacity of tomato strongly depends on the content and bioavailability of lycopene in the fruit. 
There is strong correlation between lycopene content in tomatoes and antioxidant capacity.

Occurrence    
E160d (Lycopene) is a carotenoid that occurs naturally in tomatoes.

Uses:
Carotenoid antioxidant occurring in ripe fruit, especially in tomatoes.
E160d (Lycopene) extract from tomato is intended for use as a food colour. 
E160d (Lycopene) provides the similar colour shades, ranging from yellow to red, as do the natural and synthetic lycopenes. 
E160d (Lycopene) extract from tomato is also used as a food/dietary supplement in products where the presence of lycopene provides a specific value (e.g., antioxidant or other claimed health benefits). 
The product may also be used as an antioxidant in food supplements.
E160d (Lycopene) extract from tomato is intended for use in the following food categories: baked goods, breakfast cereals, dairy products including frozen dairy desserts, dairy product analogues, spreads, bottled water, carbonated beverages, fruit and vegetable juices, soybean beverages, candy, soups, salad dressings, and other foods and beverages.

E160d (Lycopene) has been used:
in high performance liquid chromatography (HPLC) to determine its concentration in liver, kidney and lung tissue
to induce urokinase plasminogen activator receptor (uPAR) IN prostate cancer cell line
in Raman chemical imaging system to detect and visualize its internal distribution

Definition    
ChEBI: An acyclic carotene commonly obtained from tomatoes and other red fruits.

Production Methods    
E160d (Lycopene) extract from tomato is produced from a tomato variety with high lycopene content, within the range of 150 to 250 mg/kg. 
This particular variety is not generally marketed for direct consumption, but is used primarily in the production of this lycopene extract. 
The extract is produced by crushing tomatoes into crude tomato juice that is then separated into serum and pulp. 
The tomato pulp is then extracted with ethyl acetate. 
The final product is obtained after solvent removal by evaporation under vacuum at 40-60°C.

General Description    
E160d (Lycopene) is a naturally occurring red pigment, which belongs to the family of carotenoids. 
E160d (Lycopene) is found in tomatoes, watermelon and papaya. 
E160d (Lycopene) has antioxidant property.

E160d (Lycopene) is a type of organic pigment called a carotenoid. 
E160d (Lycopene) is related to beta-carotene and gives some vegetables and fruits (e.g., tomatoes) a red color.

E160d (Lycopene) is a powerful antioxidant that might help protect cells from damage. 
It's found in tomato, watermelon, red orange, pink grapefruit, apricot, rose hip, and guava.

E160d (Lycopene) is used for high blood pressure, high cholesterol, cancer, and many other conditions, but there is no good scientific evidence to support most of these uses.

E160d (Lycopene) is a plant nutrient with antioxidant properties. 
It’s the pigment that gives red and pink fruits, such as tomatoes, watermelons and pink grapefruit, their characteristic color.

E160d (Lycopene) has been linked to health benefits ranging from heart health to protection against sunburns and certain types of cancers.

This article looks at the health benefits and top food sources of lycopene.

Strong Antioxidant Properties
E160d (Lycopene) is an antioxidant in the carotenoid family.

Antioxidants protect your body from damage caused by compounds known as free radicals.

When free radical levels outnumber antioxidant levels, they can create oxidative stress in your body. This stress is linked to certain chronic diseases, such as cancer, diabetes, heart disease and Alzheimer’s.

Research shows that lycopene’s antioxidant properties can help keep free radical levels in balance, protecting your body against some of these conditions .

In addition, test-tube and animal studies show that lycopene may protect your body against damage caused by pesticides, herbicides, monosodium glutamate (MSG) and certain types of fung.

E160d (Lycopene) is a strong antioxidant that can protect your body against oxidative stress and offer some protection from certain environmental toxins and chronic diseases.

E160d (Lycopene) is a natural compound that is found in bright red fruits and vegetables like tomatoes, watermelon, and grapefruit. 
E160d (Lycopene) is a carotenoid, which are yellow, orange, or red pigments that give this color to its plants. 
E160d (Lycopene) has been linked to many health benefits, including disease prevention and protection.

Tomato products have the highest amounts of lycopene and ketchup, tomato juice, and pizza sauce are considered to be the highest sources of lycopene in an average diet for a person living in the United States, accounting for 80 percent of lycopene intake among the population.

What Is E160d (Lycopene) Used For?
One of the biggest benefits of lycopene is that it is an antioxidant and protects the body of damage from free radical stress, which can hurt DNA and other cell structures.

The antioxidant properties help balance free radical activity in the body and in doing so, may offer protection against certain diseases, keep bones strong and healthy, and help eyesight by helping delay or prevent cataracts, macular degeneration, and other age-related eye disorders.

E160d (Lycopene) is a carotenoid found in red, pink, and orange produce—especially red tomatoes. 
Like all carotenoids, lycopene is a powerful phytonutrient (aka plant nutrient) with antioxidant and anti-inflammatory properties.

E160d (Lycopene) can be found in fresh or canned fruits and vegetables, as well as snacks that have been sun-dried—though it's worth noting any food that has had its skin and/or seeds removed will contain less lycopene. 

Thermal inputs (heat) used to process tomatoes into tomato products actually increases the bioavailability of lycopene. 
Additionally, eating some fat with or around the time of your lycopene consumption is a win win, since this carotenoid is intrinsically lipid soluble.

You may also find lycopene in high-quality supplement formulas at milligram amounts (beware of sprinkling at microgram levels).

Health benefits of lycopene.
E160d (Lycopene) benefits a number of physiological systems in the body—including your eyes, heart, skin, and more.

Antioxidant properties
E160d (Lycopene) is one of the most potent plant-derived antioxidants found in fruits and vegetables. 
E160d (Lycopene) can help protect DNA, proteins, and lipids from oxidation and promotes cellular resilience and longevity by scavenging free radicals—thus, promoting redox balance.
Antioxidants help balance oxidative stress activity, creating cellular harmony in the body (and lycopene is particularly good at its job).

Heart-health benefits
Clinical research has demonstrated heart-healthy effects for lycopene intake via foods (tomatoes specifically) and targeted supplementation.
Consuming tomatoes and tomato products has yielded cardioprotective benefits, specifically, improving LDL-cholesterol, cytokine, and blood flow, while lycopene supplementation has been shown to promote a healthy systolic blood pressure.

"High dietary intake of lycopene has been shown to be beneficial for cardiovascular health," explains registered dietitian Jess Cording, M.S., R.D., CDN. 
She adds that there has been a lot of research on lycopene's ability to improve heart health in both men and women with focused cardiovascular health-support needs.

Skin benefits
At some point, you've probably been told to use a topical vitamin C or antioxidant serum on your skin to slow down natural aging and reduce fine lines and wrinkles. 
As it turns out, researchers have found that lycopene and beta-carotene are the main carotenoids (aka antioxidants) found in both skin and plasma, which explains why they're often used in skin care products. 

In addition to healthy aging and skin love, concentrated doses of lycopene also improve the body's ability to protect itself from the sun. 
If you're wondering if loading up on tomatoes during summertime is a natural replacement for sunblock, it's important to note that lycopene offers minimal sun protection (we're talking less than 2 SPF).
"E160d (Lycopene) has been shown to be helpful in protecting against sun exposure, but not to the degree where it could be considered a substitute for sunscreen and/or staying out of the sun,"* Cording specifies. 

Eye health benefits
You've probably heard that carrots are good for your eyes at some point. 
As it turns out, beta-carotene doesn't have a monopoly on that health benefit, and there's another carotenoid in town. 
Yes, lycopene (and lutein and zeaxanthin) promotes eye health and visual acuity.*  

Remember, lycopene has anti-inflammatory properties and reduces oxidative stress, which both contribute to the health and function of our eyes.
Additionally, lycopene has been shown to support vision in aging adults—so you can add this carotenoid to your longevity toolbox

Brain health benefits
Evidence shows that lycopene and other carotenoids play supporting roles in brain health and neuroprotection.
Research indicates that lycopene can promote cognition and memory, largely due to its antioxidant properties and ability to reduce oxidative stress in tissue.
Its neuroprotective effects also include helping to balance levels of cytokines (proteins that signal the immune system).

Higher dietary intake of lycopene is associated with cognitive health maintenance while aging, and many studies demonstrate this phytonutrient helps balance oxidative stress as we age as well (another reason to add lycopene to your longevity toolbox).

Bone health benefits
That's right, vitamin D and calcium shouldn't get all the credit for supporting your skeletal system—lycopene plays a role in bone health as well.

Nutritional studies show diets high in fruits and vegetables—particularly antioxidant-rich produce—have a positive effect on bone mineral status. 
Specific studies on lycopene reveal that increased lycopene intake results in increased total-body bone mineral content (BMC) and bone mineral density (BMD)—two imaging measures of bone health.
While sufficient bone mineral density is important at all ages, lycopene is an especially important phytonutrient early in life and through early adulthood (when bone accrual is at its peak), as well as later in life to keep bones strong and healthy.*

Sources of lycopene.
When it comes to food, lycopene is potent in a number of red- and pink-hued fruits and vegetables. Dietitian Leslie Bonci, MPH, R.D., LDN, loves incorporating lycopene into her diet through tomatoes and tomato products, as well as pink grapefruits, blood oranges, papaya, pink guava, red carrots, and red peppers. 
When asked for her recommendations, Cording added persimmons and red cabbage to the list. 

In addition to dietary sources, lycopene can be found in certain supplements, by itself or in multi-ingredient formulas (sometimes even in premium multivitamins). 
As nutrition scientist Ashley Jordan Ferira, Ph.D., RDN, previously shared with mbg, "E160d (Lycopene) is an eager scavenger of free radicals, an action that has global significance in the body, across multiple organ systems, every day. 
And in mbg's multi, our lycopene is extracted naturally and with care from red tomatoes (Lycopersicon esculentum)."

If you're ready to tackle the antioxidant and anti-inflammatory properties it offers, the multifaceted health benefits of lycopene are compelling enough to incorporate it into your daily supplementation routine.

While Cording says there's no official recommendation (like we have for carb, protein, fat, vitamins, and minerals) on the amount of lycopene a person should consume in a day, she notes that "current studies have shown benefits from about eight to 21 milligrams per day." 
Ferira adds, "Just like with any nutrient or phytonutrient, the dosing for lycopene is specific to the health area studied. 
But it's definitely playing in the 5-plus milligram range."*

Cording also warns that people who are taking calcium supplements should be aware that a concentrated dose of this macromineral (e.g., 500 milligrams) may decrease the absorption and bioavailability of lycopene when taken around the same time.

E160d (Lycopene) is an antioxidant that belongs to the carotenoid group. 
It’s found in high amounts in red and pink fruits, as well as dietary supplements.
E160d (Lycopene) has shown blood pressure-lowering effects and diets rich in lycopene have been associated with lower risk of some types of cancer.
E160d (Lycopene) may also have benefits for skin protection.
There is no official recommended daily intake for lycopene. 
Average intake in the United States is estimated to be about 2 milligrams of lycopene per day, which is about the amount found in a ½ cup of cherry tomatoes.
E160d (Lycopene) in the amounts found in plant sources is thought to be safe for everyone. 
Certain groups, like people on blood-thinning or blood pressure medications and pregnant women, should avoid using lycopene from dietary supplements.

THE BASICS OF LYCOPENE
E160d (Lycopene) (pronounced LIE-co-peen) is a nutrient in the carotenoid family (where you can find lutein, zeaxanthin and many others) that’s naturally found in some plants. 
E160d (Lycopene) provides the pigment that gives red and pink fruits their color and is known to have antioxidant properties. 
It’s most commonly associated with tomatoes and tomato products, which are particularly rich sources of lycopene.

 E160d (Lycopene) is a carotenoid, the bright pigment that gives red fruit and vegetables their colour, most notably in tomatoes. 
Because the tomato has seeds and grows from a flowering plant it is classed as a fruit, not a vegetable. 
There are more than 7,500 tomato varieties grown around the world and each variety contains different levels of lycopene. 
Processing fruit and vegetables releases the lycopene which is normally locked away inside the cells. 
By eating cooked fruit and vegetables, you obtain five times more lycopene than eating them raw.
 The richest dietary sources from tomatoes are ketchup, concentrated tomato purée and passata (pizza sauce) – so pizza can be good for you (although in moderation) and especially if drizzled with a little of olive oil, as lycopene is fat-soluble this can increase its absorption in our bodies.

Uses:
Scientific literature documents lycopene’s antioxidant activity and its use in cancer prevention (breast and prostate), as well as its use in the prevention of cardiovascular disease.

IUPAC NAMES:
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
Psi,psi-carotene
psi,psi-carotene

SYNONYMS:
4,4-CAROTENE
LYCOSOURCE
LYCOPENE
JARCOPENE(TM)
2,6,10,14,19,23,27,31-OCTAMETHYL-DOTRIACONTA-2,6,8,10,12,14,16,18,20,22,24,26,30-TRIDECAENE
PSI,PSI-CAROTENE
Y,Y-CAROTENE
E 160d
E160d (Lycopene) (90%)
Redivivo (E160d (Lycopene)) 10% CWS/S-TG
Redivivo (E160d (Lycopene)) 10% FS
Redivivo (E160d (Lycopene)) 10% WS
Redivivo (E160d (Lycopene)) 5% TG/P
Lycored
MexorylSAQ
Natural E160d (Lycopene)
ToMata color
E160d (Lycopene), dispersion
E160d (Lycopene), Redivivo
E160d (Lycopene) oil
E160d (Lycopene) Powder
Herba Lophateri
Lycoypene
Nano Liposomal lycopene from tomato
The tomato extracts
E160d (Lycopene) 502-65-8
(all-E)-2,6,10,14,19,23,27,31-Octamethyl-2,6,8,10,12,14,16,18,20,22,24,26,30-dotriacontatridecaene
Soluble LYCOPENE, Liposomal LYCOPENE, LYCOPENE NanoEmulsion, NanoActive LYCOPENE
lycopene from tomato
CI 75125
LYCOPENE WITH TLC
LYCOPENE FROM TOMATOES
LYCOPENE POWDER EXTRACT 5%
LYCOPENE (NATURAL YELLOW 27)
LYCOPENE FROM TOMATO 90% FOOD GRADE
Lycopin
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
LYCOPENE SNAP-N-SHOOT 0.1mg/mL(P)
LYCOPENE10CWD
LYCOPENE(SYNTHETIC)
FORMULATEDLYCOPENE
LYCOVIT
TRANS-LYCOPENE
SYNTHETICCRYSTALLINELYCOPENE
ALL-TRANS-LYCOPENE
Lycopen
2,6,10,14,19,23,27,31-Octamethyl-dotriacont2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
ω,ω-Carotene, 2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriacontane-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
E160d (Lycopene) (Natural)
LyocpenePowder
E160d (Lycopene),ψ,ψ-Carotene, 2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
E160d (Lycopene) (Standard)
E160d (Lycopene) fandachem
E160d (Lycopene), Redivivo(TM)
E160d (Lycopene) USP
E160d (Lycopene) USP/EP/BP
LYCOPENE/CAS:502-65-8