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CAS Number:472-93-5
CHEBI:27740
PubChem CID: 5280791
UNII: DH369M0SOE
CompTox Dashboard (EPA): DTXSID70897429
Gamma-Carotene is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants.
Gamma-Carotene is formed from cyclization of lycopene by lycopene cyclase epsilon.
Along with several other carotenoids, γ-Carotene is a vitamer of vitamin A in herbivores and omnivores.
Carotenoids with a cyclized, beta-ionone ring can be converted to vitamin A, also known as retinol, by the enzyme Beta-carotene 15,15'-dioxygenase; however, the bioconversion of gamma-carotene to retinol has not been well-characterized.
Gamma-carotene is a cyclic carotene obtained by the cyclisation of lycopene.
Gamma-Carotene has a role as a plant metabolite and a fungal metabolite.
Gamma-Carotene is a cyclic carotene and a carotenoid beta-end group.
gamma-Carotene is a natural product found in Flavobacterium, Equisetum arvense, and other organisms with data available.
Gamma-Carotene is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants.
Gamma-Carotene is formed from cyclization of lycopene by lycopene cyclase epsilon.
Along with several other carotenoids, γ-Carotene is a vitamer of vitamin A in herbivores and omnivores.
General description of Gamma-carotene
Carotene is a plant carotenoid with provitamin A activity.
Definition of Gamma-carotene
Gamma-Carotene is a cyclic carotene obtained by the cyclisation of lycopene.
Gamma-Carotene is a plant carotenoid with provitamin A activity.
What is Gamma-carotene?
Gamma-carotene is the most abundant form of carotene.
Generally, it consists of 40 carbons arranged into eight isoprene units with beta-rings at both ends of the molecule.
Significantly, Gamma-carotene causes the red-orange pigmentation in plants and fruits.
Basically, some of the richest sources of beta carotene include Vietnamese gac, crude palm oil, mangoes, pumpkin, papayas, cantaloupe, root vegetables such as carrots, sweet potatoes, etc.
Also, leafy vegetables such as spinach, kale, etc. For instance, Vietnamese gac and palm oil are the richest sources of beta carotene, containing amounts ten times higher than carrot.
Applications of Gamma-carotene
Carotene may be used as a reference standard in the determination of Gamma-carotene in fruits using high performance liquid chromatography coupled with diode array detector and mass spectrometry.
Uses of Gamma-carotene
Gamma-Carotene may be used as a reference standard in the determination of Gamma-carotene in fruits using high performance liquid chromatography coupled with diode array detector and mass spectrometry.
Gamma-carotene both have antioxidant features, but β-carotene has notably more antioxidant potential than retinol.
Gamma-carotene is able to scavenge hydroxyl radical, superoxide anion, and peroxynitrite.
In addition, it extinguishes singlet oxygen and so prevents lipid peroxidation.
Gamma-carotene can also bind to transition metals, preventing them from catalyzing the production of radical oxygen species.
Both retinol and Gamma-carotene work as chain-breaking antioxidants in the process of lipid peroxidation.
However, Gamma-carotene activity is only observed at low partial pressures of oxygen.
At higher oxygen pressures, carotenoids and retinoids lose their chain-breaking property and instead indicate an autocatalytic, prooxidant effect.
Gamma-carotene also potentiates the antioxidant impacts of ascorbic acid.
Colors
The yeasts have been used as sources of a number of carotenoids for use as food colorants such as astaxanthin, β-carotene and Gamma-carotene, lycopene, lutein, torulene, torularhodin, and zeaxanthin.
For instance, Phaffia rhodozyma and Xanthophyllomyces dendrorhous have been used in industrial-scale production of the carotenoid astaxanthin.
Gamma-carotene can be used for aquafeed as a colorant or as an immunostimulant in food or in poultry, fish, or mammalian feed.
Other colorants produced by yeast fermentation are riboflavin and caramel colors produced from the processing of yeast extracts.
Gamma-carotene and cancer
It has been shown in trials that the ingestion of beta carotene at about 30 mg/day from synthetic supplements increases the rate of lung cancer and prostate cancer, and increases mortality in smokers and people with a history of asbestos exposure.
Beta-carotene consumed as part of whole foods has no such observably negative effects
A randomised trial into the use of Gamma-carotene and vitamin A for prevention of lung cancer had to be stopped early due to the apparent increase in the incidence of lung cancer in those with lung irritation from smoking or asbestos exposure.
A review of all randomized controlled trials in the scientific literature by the Cochrane Collaboration published in JAMA in 2007 found that Gamma-carotene increased mortality by 5%.
Gamma-carotene and Cognition
A recent report demonstrated that 50mg of Gamma-carotene every other day prevented cognitive decline in a study of over 4000 physicians at a mean treatment duration of 18 years.
Prevention of vitamin A deficiency
Approximately 50 members of the carotenoid family can be converted into retinol, an active form of vitamin A.
Intake of these carotenoids, referred to as provitamin A compounds, can help to prevent vitamin A deficiency.
The most common consumed provitamin A carotenoids in the North American diet include Gamma-carotene, alpha-carotene, beta-crpytoxanthin, gamma-carotene, lycopene, lutein, zeaxanthin, and astaxanthin.
Until late in the 20th century, the vitamin A activity of carotenoids was researchers' main focus when it came to investigating the health benefits of these phytonutrients.
Antioxidant & immune-enhancing activity
Carotenoids have potent antioxidant activity, enabling them to protect cells from free radical damage.
Additionally, carotenoids, notably Gamma-carotene, are also suggested to play a role in supporting immune system function.
Due to these actions, carotenoids have received a great amount of attention as potential anti-cancer and anti-aging compounds.
Enhancing proper cell communication
Gamma-carotene has also been shown to stimulate cell-to-cell communication.
Since researchers now believe that poor cell-to-cell communication may be one of the factors leading to proliferation of cells, a condition that eventually leads to cancer, Gamma-carotene may play an important role in cancer prevention.
Supporting female reproductive system
Gamma-carotene is also believed to play a role in female reproduction, although their exact function has yet to be determined.
This hypothesis is partially based upon the finding that the corpus luteum has the highest concentration of beta-carotene of any organ in the body.
Biochem/physiol Actions of Gamma-carotene
Metabolite in carotenoid biosynthesis and the biosynthesis of plant secondary metabolites.
Purification Methods of Gamma-carotene
Purify γ-carotene by chromatography on alumina, or magnesia columns.
When crystallised from *C6H6/MeOH (2:1), it had m 177.5o.
Store it in the dark, under an inert atmosphere at 0o, or in an evacuated tube at -20o.
The purity is verified by TLC on Ca(OH)2/Kieselgel (8:2) using pet ether (b 60-80o) as eluant.
Alpha vs Gamma-carotene
Moreover, Gamma-carotene is a type of carotenoid the precursor or the inactive form of vitamin A.
Basically; carotenoids are plant pigments hue in many fruits and vegetables while being responsible for their yellow, red, and orange color.
Significantly, they are antioxidants, which serve as strong cancer-fighting agents.
For instance, the two types of carotenoids are carotene and xanthophylls.
Also, the other two types of provitamin A carotenoids include alpha carotene, which is a carotene same as beta carotene and beta-cryptoxanthin, which is a xanthophyll.
In the meanwhile, beta carotene provides the protection against sunlight while lowering the risk of metabolic syndrome and lung cancer.
However, in smokers and former asbestos workers, beta carotene increases the risk of lung cancers.
Record Information of Gamma-carotene
Secondary Accession Numbers: None
Metabolite Identification
Common Name: gamma-Carotene
Description
gamma-Carotene is a cyclic carotene obtained by the cyclization of lycopene.
Gamma-carotene is found in human serum and breast milk.
Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea.
Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds.
Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans.
This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet.
Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer.
Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important.
TECHNICAL DATA of Gamma-carotene
CAS No: 472-93-5
Product Code: FC32341
Chemical Formula:C40H56
Molecular Weight:536.87 g/mol
Properties of Gamma-carotene
Chemical formula: C40H56
Molar mass: 536.888 g·mol−1
Melting point: 160 to 162 °C (320 to 324 °F; 433 to 435 K)
Computed Properties of Gamma-carotene
Molecular Weight: 536.9
XLogP3: 14.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count;: 13
Exact Mass: 536.438201786
Monoisotopic Mass: 536.438201786
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 40
Formal Charge: 0
Complexity: 1180
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 10
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Physical Properties of Gamma-carotene:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 261.00 °C. @ 760.00 mm Hg
Soluble in:water, 1.054e-013 mg/L @ 25 °C (est)
Gamma-carotene Properties
Melting point:152-153.5°; mp 177.5°
Boiling point:644.94°C
Density 0.9380
refractive index 1.5630
storage temp. -20°C
SPECIFICATIONS & PROPERTIES of Gamma-carotene
Min. Purity Spec:93%
Physical Form (at 20°C):Yellow-red to dark red to red-brown powder
Melting Point: 157-163°C
Flash Point: 103°C
Density: 1
Long-Term Storage: Store long-term at -20°C
Background of Gamma-carotene
Gamma-carotene is a carotenoid.
Carotenoids are red, orange, or yellow, fat-soluble compounds.
These compounds are naturally present in many fruits, grains, oils, and vegetables.
Alpha, beta, and gamma carotene are considered provitamins because they can be converted to active vitamin A.
Commercially available beta-carotene is man-made or taken from palm oil, algae, or fungi.
Gamma-carotene is converted to retinol, which is essential for vision and growth.
Studies in humans show that beta-carotene has promising use for oral leukoplakia (pre-cancerous mouth lesions) and for sunburn.
However there was a lack of benefit for sun damaged skin, mole prevention, heart disease risk, infection with H. Pylori, cataract prevention, diabetes, and stroke.
Research shows that Gamma-carotene increased the risk of bladder, lung, stomach, and prostate cancer.
Also the general incidence of cancer in asbestos workers, smokers, or high risk individuals increased.
Additionally, some research suggested increased risk of heart disease and death with Gamma-carotene supplementation.
IDENTITY
CAS Number:472-93-5
MDL Number:MFCD00001556
MF:C40H56
MW:536.87
EINECS: 230-636-6
Carotenemia of Gamma-carotene
Carotenemia or hypercarotenemia is excess carotene, but unlike excess vitamin A, Gamma-carotene is non-toxic.
Although hypercarotenemia is not particularly dangerous, it can lead to a yellowing of the skin (carotenodermia).
Hypercarotenemia is most commonly associated with consumption of an abundance of carrots, but it also can be a medical sign of more dangerous conditions.
Production OF Gamma-carotene
Most of the world's synthetic supply of carotene comes from a manufacturing complex located in Freeport, Texas and owned by DSM.
The other major supplier BASF also uses a chemical process to produce beta carotene.
Toghether these suppliers accound for about 85% of the beta carotene on the market.
In Spain Vitatene produces natural beta carotene from Blakeslea trispora, as does DSM but at much lower amount when compared to its synthetic beta carotene operation.
In Australia, organic beta-carotene is produced by Aquacarotene Limited from dried marine algae Dunaliella salina grown in harvesting ponds situated in Karratha, Western Australia.
Gamma-carotene is also found in palm oil, corn, and in the milk of Guernsey dairy cows, causing their milk to turn yellow.
Total synthesis OF Gamma-carotene
There are currently two commonly used methods of total synthesis of Gamma-carotene.
The first was developed by the Badische Anilin- & Soda-Fabrik (BASF) and is based on the Wittig reaction.
The second is a Grignard reaction, elaborated by Hoffman-La Roche from the original synthesis of Inhoffen et al.
They are both symmetrical; the BASF synthesis is C20 + C20 , and the Hoffman-La Roche synthesis is C19 + C2 + C19.
Property OF Gamma-carotene
Formula C40H56
Weight 536.873 [g/mol]
Complexity: 1176.27
XLogP: 10.10
TPSA: 0.00
#HDonors: 0
#HAcceptors: 0
Gibbs Energy: 292.3 [kcal/mol]
EXPLANATION OF Gamma-carotene
The Committee did not undertake a general re-evaluation of beta-carotene for use as a colouring agent but focused its assessment on the production and analytical characteristics of beta-carotene from Blakeslea trispora.
Gamma-carotene is obtained from B. trispora by co-fermentation of the two sexual types of the fungus in specific proportions.
Both types are stable in cultures maintained under conditions consistent with good manufacturing practice.
These source organisms are neither pathogenic nor toxinogenic.
Gamma-carotene is isolated from the fungal biomass by solvent extraction and crystallized.
The main articles of commerce are suspensions in food-grade vegetable or plant oil and water-dispersible powders.
These formulations are made for ease of use and in order to improve stability, as carotenes easily oxidize.
As in synthetic beta-carotene, the colouring principle of beta-carotene from B. trispora consists predominantly of all-trans Gamma-carotene.
The content of total colouring matter is not less than 96% (expressed as beta-carotene).
Gamma-carotene from B. trispora may also contain other carotenoids, of which gamma-carotene accounts for the major part, at concentrations up to 3%.
Gamma-carotene occur naturally in carotenoid-containing vegetables.
Similarities Between Alpha and Gamma-carotene
Alpha and Gamma-carotene are two types of unsaturated hydrocarbons, serving as precursors to vitamin A synthesis.
Both have the molecular formula, C40H56.
They do not contain oxygen atoms.
Plants exclusively synthesize these carotenes.
But, animals excluding some aphids and spider mites are unable to synthesize them. However, some fungi synthesize carotene.
Both are photosynthetic pigments, absorbing ultraviolet, violet, and blue light while scattering red or orange and yellow light.
Therefore, they are responsible for the colors of many fruits, vegetables, an fungi.
Abundance
Gamma-carotene is the second most abundant form of carotene, while beta carotene is the most abundant form of carotene.
Retinyl Groups
Gamma-carotene contains a single retinyl group while beta carotene contains two retinyl groups.
As a Precursor of Vitamin A
Gamma-carotene produces 50% of vitamin A as beta carotene does while beta carotene is the most powerful carotene, which produces vitamin A in the small intestine.
Dietary Sources
Gamma-carotene is more abundant in yellow-orange vegetables such as carrots, sweet potatoes, pumpkin, etc. and dark-green vegetables such as broccoli, spinach, green beans, green peas, etc. In contrast, beta carotene is rich in Vietnamese gac, crude palm oil, cantaloupe, mangoes, pumpkin, and orange root vegetables such as carrot and sweet potatoes.
Heath Benefits of Gamma-carotene
The high levels of Gamma-carotene are associated with cancer death, cardiovascular disease, death from diabetes, etc. while beta carotene provides the protection against sunlight while lowering the risk of metabolic syndrome and lung cancer.
Entry of Gamma-carotene
C05435
Name: gamma-Carotene
Formula : C40H56
Exact mass: 536.4382
Mol weight: 536.8726
While the metabolisms of prominent hydrocarbon carotenoids such as lycopene and beta-carotene have been extensively studied, the functional role of gamma-carotene remains unexplored.
Because the chemical structure of gamma-carotene is a hybrid of lycopene and beta-carotene, the total synthesis of the analogous metabolite of gamma-carotene 2,6-cyclo-gamma-carotene-1,5-diol was undertaken.
The total synthesis 2,6-cyclo-gamma-carotene-1,5-diol was accomplished using a C15+C10+C15 Wittig coupling strategy.
Description of Gamma-carotene
Gamma-carotene, also known as γ-carotene, is a member of the class of compounds known as carotenes.
Carotenes are a type of unsaturated hydrocarbons containing eight consecutive isoprene units.
They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain.
Carotenes belonging form a subgroup of the carotenoids family.
Gamma-carotene can be found in a number of food items such as corn, yellow bell pepper, fig, and papaya, which makes gamma-carotene a potential biomarker for the consumption of these food products.
Properties of Gamma-carotene
Water Solubility: 0.00038 g/L
logP: 9.59
logP: 11.53
logS: -6.2
Physiological Charge: 0
Hydrogen Acceptor Count: 0
Hydrogen Donor Count: 0
Polar Surface Area. 0 Ų
Rotatable Bond Count: 13
Refractivity: 194.71 m³·mol⁻
Polarizability: 69.79 ų
Number of Rings: 1
Bioavailability: No
Rule of Five: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No
Classification of Gamma-carotene
Description
Belongs to the class of organic compounds known as carotenes.
Gamma-carotene are a type of unsaturated hydrocarbons containing eight consecutive isoprene units.
Gamma-carotene by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain.
Carotenes belonging form a subgroup of the carotenoids family.
Kingdom Organic compounds
Super Class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub Class: Tetraterpenoids
Direct Parent: Carotenes
Alternative Parents
Branched unsaturated hydrocarbons
Cycloalkenes
Unsaturated aliphatic hydrocarbons
Substituents
Carotene
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound
Molecular Framework: Aliphatic homomonocyclic compounds
Gamma-carotene
Gamma-carotene is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants.
Gamma-carotene is formed from cyclization of lycopene by lycopene cyclase epsilon. Along with several other carotenoids, Gamma-carotene is a vitamer of vitamin A in herbivores and omnivores.
Carotenoids with a cyclized, beta-ionone ring can be converted to vitamin A, also known as retinol by the enzyme Beta-carotene 15,15'-dioxygenase, however, the bioconversion of gamma-carotene to retinol has not been well-characterized.
Supplement Fac of Gamma-carotene
Gamma-carotene is converted by the body to vitamin A as needed.
Vitamin A is essential for vision, growth, cellular differentiation and proliferation, and the integrity of the immune system.
Gamma-carotene is also a major component of the body's natural antioxidant defenses against free radicals
Synonyms of Gamma-carotene
GAMMA-CAROTENE
beta,psi-Carotene
472-93-5
UNII-DH369M0SOEDH369M0SOE
2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaenyl]-1,3,3-trimethylcyclohexene
gamma-Carotin
gamma-Carotene, all-trans-
CHEBI:27740
DTXSID70897429
gamma-Carotene, >=90% (HPLC)
ZINC8219952
LMPR01070260
C05435
Q5520255
