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E160c (Capsorubin)

CAPSORUBIN

CAS Number: 470-38-2
EC Number: 207-425-2
Chemical formula: C40H56O4


E160c (Capsorubin) is a natural red dye of the xanthophyll class. 
As a food coloring, E160c (Capsorubin) has the E number E160c(ii). 
E160c (Capsorubin) is a carotenoid found in red bell pepper (Capsicum annuum) and a component of paprika oleoresin. 
E160c (Capsorubin) is also found in some species of lily.
E160c (Capsorubin) is a carotenone.


E160c (Capsorubin) is a natural product found in Lilium pumilum, Nephroma arcticum, and other organisms with data available.
E160c (Capsorubin) belongs to the class of organic compounds known as triterpenoids.
These are terpene molecules containing six isoprene units. 
Thus, E160c (Capsorubin) is considered to be an isoprenoid.
E160c (Capsorubin) is a carotenoid that has been found in C. annuum and has diverse biological activities.


E160c (Capsorubin) is a natural red dye of the xanthophyll class. 
As a food coloring, E160c (Capsorubin) is a carotenoid found in red bell pepper and a component of paprika oleoresin.
E160c (Capsorubin), is a carotenoid pigment. 
E160c (Capsorubin) is also a metabolite of a Xanthophyll (X742000) with a structure containing unusual five-membered ring end groups. 
E160c (Capsorubin) is found in red peppers (Capsicum annuum), which has shown to have Antioxidant, Antinociceptive, and Anti-inflammatory effects.


Extraction of E160c (Capsorubin):
From paprika extract, another red coloring substance capsorubin (C40H60O4; mp 201 °C) can also be isolated. 
E160c (Capsorubin) crystallizes from a mixture of benzene and petrol in violet-red needles. 
From carbon disulphide, the dye is obtained in rhombic plates. 
It is readily soluble in alcohol and acetone, sparingly soluble in ether, benzene, and carbon disulphide, and almost insoluble in petroleum ether. 
The chromatographic behavior of capsorubin is similar to that of capsanthin.


For extraction of capsorubin, paprika pods are pre-treated with ethanol, and then extracted with petroleum ether. 
The combined extracts are concentrated in vacuum and the dye is chromatographed on calcium carbonate. 
After repeated chromatographic absorption, the capsorubin ester is saponified with methanol potassium hydroxide, and the dye is finally chromatographed repeatedly on calcium carbonate from carbon disulphide solution. 
For further purification, the dye is crystallized from the mixture of benzene and petrol. 
The yield of pure dye is about 260 mg from 1 kg of pods. 
Recently, paprika oleoresin has been extracted by supercritical carbon dioxide method.

USES and APPLICATIONS of CAPSORUBIN:
-E160c (Capsorubin) is a carotenoid that has been found in C. annuum and has diverse biological activities. 
-E160c (Capsorubin) inhibits lipid peroxidation induced by 2,2'-azobis(2,4-dimethyl valeronitrile) (AMVN) in vitro when used at a concentration of 167 µM. 
-E160c (Capsorubin) (1 µM) decreases UVB-induced formation of DNA strand breaks and apoptosis in isolated human dermal fibroblasts.
-Dye, gives orange-red color.


-In addition, an antioxidant component, the so-called "scavenger of free radicals", has anti-wrinkle and stimulating properties, prevents loss of firmness and smoothness of the skin, prevents inflammation, blackheads and blackheads, strengthens the skin and hair bulbs, is a precursor of vitamin A. 
-E160c (Capsorubin) also helps in the elimination of scars and stretch marks, improves skin tone, strengthens skin against external factors, sun, allergens and pollution.
-E160c (Capsorubin) is most often found in colored lipsticks and lip glosses, bronzing and self-tanning cosmetics and sunscreens.

ALTERNATIVE PARENTS of CAPSORUBIN:
-Cyclopentanols 
-Enones 
-Acryloyl compounds 
-Ketones 
-Cyclic alcohols and derivatives 
-Organic oxides 
-Hydrocarbon derivatives 

SUBSTITUENTS of CAPSORUBIN:    
-Triterpenoid
-Cyclopentanol
-Alpha,beta-unsaturated ketone
-Enone
-Cyclic alcohol
-Acryloyl-group
-Secondary alcohol
-Ketone
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Carbonyl group
-Alcohol
-Aliphatic homomonocyclic compound

PHYSICAL and CHEMICAL PROPERTIES of CAPSORUBIN:
Molar mass: 600.884 g·mol−1
Melting point: 201 °C (394 °F; 474 K)
Water Solubility: 0.00073 g/L    
logP: 7.43    
logP: 8.66    
logS: -5.9    
pKa (Strongest Acidic): 14.91    
pKa (Strongest Basic): -2.7    
Physiological Charge: 0    
Hydrogen Acceptor Count: 4    
Hydrogen Donor Count: 2    
Polar Surface Area: 74.6 Ų    


Rotatable Bond Count: 12    
Refractivity: 194.98 m³·mol⁻¹    
Polarizability: 74.42 ų    
Number of Rings: 2
Assay:    95.00 to 100.00
Food Chemicals Codex Listed:    No
Boiling Point:    741.80 °C. @ 760.00 mm Hg (est)
Flash Point:    782.00 °F. TCC ( 416.40 °C. ) (est)
logP (o/w):    7.970 (est)
Soluble in: water, 2.839e-008 mg/L @ 25 °C (est)


Appearance:
Form: Crystalline
Color: Not determined.
Odor: Characteristic
Structural Formula C40H56O4
Molecular Weight 600.9 g/mol
Odor threshold: Not determined.
pH-value: Not applicable.


Change in condition:
Melting point/Melting range: Undetermined.
Boiling point/Boiling range: Undetermined.
Flash point: Not applicable.
Flammability (solid, gaseous): Product is not flammable.
Decomposition temperature: Not determined.
Auto igniting: Not determined.
Danger of explosion: Product does not present an explosion hazard.
Explosion limits:
Lower: Not determined.
Upper: Not determined.


Vapor pressure: Not applicable.
Density: Not determined.
Relative density Not determined.
Vapor density Not applicable.
Evaporation rate Not applicable.
Solubility in / Miscibility with
Water: Not determined.
Partition coefficient (n-octanol/water): Not determined.
Viscosity:
Dynamic: Not applicable.
Kinematic: Not applicable.

FIRST AID MEASURES of CAPSORUBIN:
-Description of first aid measures
*General information: 
No special measures required.
*After inhalation: 
Supply fresh air; consult doctor in case of complaints.
*After skin contact: 
Generally the product does not irritate the skin.
*After eye contact: 
Rinse opened eye for several minutes under running water.
*After swallowing: 
If symptoms persist consult doctor.

-Indication of any immediate medical attention and special treatment needed:
No further relevant information available.

ACCIDENTAL RELEASE MEASURES of CAPSORUBIN:
-Personal precautions, protective equipment and emergency procedures: Not required.
-Environmental precautions: Do not allow to enter sewers/ surface or ground water.
-Methods and material for containment and cleaning up: Pick up mechanically.

FIRE FIGHTING MEASURES of CAPSORUBIN:
-Extinguishing media:
Suitable extinguishing agents:
Use fire fighting measures that suit the environment.
-Advice for firefighters:
-Protective equipment: No special measures required.

EXPOSURE CONTROLS/PERSONAL PROTECTION of CAPSORUBIN:
-Additional information about design of technical systems: No further data.
-Control parameters:
*Components with limit values that require monitoring at the workplace: Not required.
*Additional information: The lists that were valid during the creation were used as basis.

-Exposure controls:
*Personal protective equipment:
*General protective and hygienic measures:
The usual precautionary measures for handling chemicals should be followed.
*Breathing equipment: Not required.

*Protection of hands:
The glove material has to be impermeable and resistant to the product/ the substance/ the preparation.
*Eye protection: Not required

HANDLING and STORAGE of CAPSORUBIN:
-Handling:
Precautions for safe handling:
No special measures required.

-Information about protection against explosions and fires: 
No special measures required.
Conditions for safe storage, including any incompatibilities:

-Storage:
*Requirements to be met by storerooms and receptacles: 
No special requirements.
*Information about storage in one common storage facility: 
Not required.
*Further information about storage conditions: None.
-Specific end use(s): 
No further relevant information available.

STABILITY and REACTIVITY of CAPSORUBIN:
-Reactivity: No further relevant information available.
-Chemical stability:
-Possibility of hazardous reactions: No dangerous reactions known.
-Conditions to avoid: No further relevant information available.

SYNONYMS:
(3S,5R,3′S,5′R)-3,3'-Dihydroxy-κ,κ-carotene-6,6′-dione
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-Bis[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa 2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
(3S,3'S,5R,5'R)-3,3'-Dihydroxy-kappa,kappa-carotene-6,6'-dione
(3S,3'S,5R,5'R)-3,3'-Dihydroxy-κ,κ-carotene-6,6'-dione 
(3S,5R,3'S,5'R)-3,3'-Dihydroxy-k,k-carotene-6,6'-dione
(3S,5R,3's,5'r)-3,3'-Dihydroxy-kappa,kappa-carotene-6,6'-dione    
(3S,5R,3'S,5'r)-3,3'-dihydroxy-kappa,kappa-carotene-6,6'-dione    
3,3'-Dihydroxy-K,K-carotene-6,6'-dione    
3,3'-Dihydroxy-k,k-carotene-6,6'-dione    
3,3'-Dihyroxy-kappa,kappa-carotene-6,6'-dione    
all-trans-E160c (Capsorubin)
e160 (E160c (Capsorubin))    
E160 (E160c (Capsorubin))
2,4,6,8,10,12,14,16,18-Eicosanonaene-1,20-dione, 1,20-bis(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethyl-, (1R,1R,4S,4S)-(all-E)-
E160c (Capsorubin), all-trans-
all-trans-E160c (Capsorubin)
κ,κ-Carotene-6,6′-dione, 3,3′-dihydroxy-, (3S,3′S,5R,5′R)-

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