CAPSANTHIN

CAPSANTHIN = PAPRIKA EXTRACT = CAPSORUBIN

CAS Number: 465-42-9
EC-Number: 207-364-1
MDL Number: MFCD03423725
Molecular Formula: C40H56O3

Capsanthin is a carotenone. 
Capsanthin has a role as a plant metabolite.
Capsanthin is a natural product found in Lilium lancifolium and Gallus gallus with data available.
Capsanthin is a natural red dye of the xanthophyll class of carotenoids. 
Capsanthin is a natural carotenoid isolated from red paprika.

As a food coloring, Capsanthin has the E number E160. 
Capsanthin is the main carotenoid in the Capsicum annuum species of plants including red bell pepper, New Mexico chile, and cayenne peppers (Capsicum annuum) and a component of paprika oleoresin. 
Capsanthin is also found in some species of lily. 
Among other carotenoids, capsanthin is considered to have the greatest antioxidant capacity due to the presence of eleven conjugated double bonds, a conjugated keto group, and a cyclopentane ring.

Constituent of paprika (Capsicum annuum) and asparagus (Asparagus officinalis). 
Capsanthin is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids). 
Capsanthin is found in many foods, some of which are italian sweet red pepper, red bell pepper, herbs and spices, and pepper (c. annuum).

Capsanthin belongs to the class of organic compounds known as xanthophylls. 
These are carotenoids containing an oxygenated carotene backbone. 
Carotenes 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. 
Xanthophylls arise by oxygenation of the carotene backbone.

Capsanthin, the red xanthophyll pigment, is used as a food additive approved by the European Union (EU) under the name as E160c. 
The common names for E160c are paprika extract, capsanthin or capsorubin. 
Capsanthin shows potent anti-adipogenic, lipolytic and fatty acid burning activities due to Capsanthin's potent adrenoceptor-beta2-agonistic activity. 
Capsanthin was revealed, that capsanthin was not a thermogenic substance that is why Capsanthin may be a good candidate for the development of new bioactive agent effective as a new anti-obese or insulin sensitivity enhancing substance.

Capsanthin is a carotenoid, just like beta-carotene, lycopene, lutein and zeaxanthin. 
These pigments, found in red, orange, yellow, and green fruits and vegetables, are recognized for their ability to provide antioxidant protection to the eye and to promote eye health. 
Some carotenoids, like cryptoxanthin, are also precursors to vitamin A, which means they help the body produce this vision-supporting vitamin.

Capsanthin (Paprika Oleoresin/Capsorubin) is manufactured from the dried and ground sweet pepper pods of Capsicum Annum. 
The colorings that impart the characteristics yellow to orange hue of paprika are Capsanthin and Capsorubin. 
This red spice imparts flavor and the color of food, paprika color compounds can also be solvent extracted to produce paprika oleoresin, a purified form of the coloring compounds.
Capsanthin, also known as the red pepper carotenoid, is one of the major color pigments of paprika oleoresin, an oil-soluble extract, isolated from the fruits of Capsicum annum Linn or Capsicum frutescens. 

Capsanthin is the major colouring compounds contained in the Paprika oleoresin, which is a kind of oil-soluble extract isolated from the fruits Capsicum annuum or Capsicum frutescens, and is a colouring and/or flavouring in food products. 
As a pink pigment, Capsanthin is very abundant in peppers, accounting for 60% of the proportions of all flavonoids in the peppers. 
Capsanthin is a carotenoid that has been found in annuum and has diverse biological activities.

Capsanthin is a natural, fat-soluble, red pigment of the xanthophyll class. 
Capsanthin is one of the main carotenoid in red bell pepper (Capsicum annuum). 
Capsanthin is European Union (EU) approved food additive under the name as E160c. 
Capsanthin is used as a natural coloring agent in food and drinks.

Capsanthin, derived from Capsicum annuum (or chili pepper), is a bioactive carotenoid that delivers a more holistic range of benefits than other eye health solutions by addressing both short- and long-term eye health.
The species Capsicum annuum L. is used to manufacture a paprika extract for food coloration. 
Carotenoids, such as capsanthin and capsorubin, are the main compounds responsible for the red color. 
It is a natural red dye of the xanthophyll class.

Capsanthin is a natural red dye of the xanthophyll class of carotenoids. 
As a food coloring, Capsanthin has the E number E160c(i). 
Capsanthin is the main carotenoid in the Capsicum annuum species of plants including red bell pepper, New Mexico chile, and cayenne peppers (Capsicum annuum) and a component of paprika oleoresin. 
Capsanthin is also found in some species of lily.
Among other carotenoids, capsanthin is considered to have the greatest antioxidant capacity due to the presence of eleven conjugated double bonds, a conjugated keto group, and a cyclopentane ring.

Capsanthin is a carotenoid found in red paprika that has diverse biological activities.
Carotenoids are natural red, orange, and yellow pigments found in many fruits, vegetables, and spices, such as carrots and squash. 
Carotenoids support eye health, which may be the reason carrots have long had a reputation for supporting healthy vision. 
Capsanthin is a specific kind of Carotenoid that gives red bell peppers, chili peppers, cayenne peppers, and paprika their bright red hue. 
These foods have been part of the human diet for thousands of years.

Carotenoids, including Capsanthin, are fat-soluble pigments that have antioxidant properties.
There are more than 750 Carotenoids found in plants, algae, and photosynthetic bacteria; however only 20 of these are found in the human body.

Extraction of Capsanthin:
Paprika pods without shells and seeds are dried at 35–40 °C. 
The finely ground material is then extracted at room temperature. 
The solution is diluted with a threefold volume of ether, and 30% methanol potassium hydroxide is added, and then the mixture is allowed to settle for 1–2 days at room temperature. 

After that, the free phytoxanthins are dissolved in ether. 
The solution is washed, until it shows a neutral reaction, dried over sodium sulphate and most of the solvent is evaporated under reduced pressure. 
The ethereal residue is diluted with much petroleum ether and allowed to settle in cold for 24 h. 
In this way, about 1.2–2 g of crude capsanthin is obtained from 1 kg of high quality paprika. 

The crude capsanthin is the mixture of esters of capsanthin, capsorubin, zeaxanthin, cryptoxanthin, carotenoids, violaxanthin, and cryptocapsin. 
Capsanthin is separated out from other carotenoids by chromatography on calcium carbonate or zinc carbonate. 
Carbon disulphide is employed as solvent for developing the chromatograph. 
A mixture of benzene and ether (1:1) is also suitable for this purpose.

USES and APPLICATIONS of CAPSANTHIN:
-Potential nutriceutical Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. 
-Capsanthin Inhibits adipogenesis in 3T3-L1 preadipocytes. 
-Capsanthin is a natural carotenoid compound.

-Capsanthin is a carotenoid originally found in Capsicum that exhibits anticancer and chemopreventive activities.
-In leukemia cells, Capsanthin upregulates expression of PPARγ, Nrf2, and p21, downregulates expression of cyclin D1, induces apoptosis, and inhibits cellular proliferation. 
-Capsanthin may be used as an analytical reference standard for the quantification of the analyte in red pepper powder, red pepper fruits, paprika and oleoresin using chromatography techniques.
-Antineoplastic

-Capsanthin is widely used as a color additive in food industries across the globe. 
-The photoprotective effect of Capsanthin protects human dermal fibroblasts against UVB induced DNA damage.
-Capsanthin has antioxidant properties, being able to help the body to scavenge the free radicals as well as inhibiting the growth of cancer cells.
-Capsanthin reduces hydrogen peroxide-induced production of reactive oxygen species (ROS).
-Capsanthin is also able to support eye health and recent research has revealed its unique ability to help maintain intraocular pressure within a healthy range. 

-Capsanthin is rich in beta-carotene and vitamin C, so Capsanthin has the function of health care.
-Capsanthin is widely used in aquatic products, meat, pastries, salads, canned food, beverage and other various types of food and medicine coloring.
-Capsanthin also can be used for cosmetics production.
-Capsanthin with high security, heat, light, free from the environment PH value and impact of metal ions can be widely used in aquatic products, meat, pastries, salads, canned food, beverages and other food, beverages, cosmetics as a coloring agent in the pharmaceutical industry as intermediates.

-Capsanthin is a natural carotenoid extracts of pepper. 
Capsanthin is used as natural colorant and anti-oxidant. 
-Capsanthin is the most sought after natural ingredient in food and beverage coloring applications. 
Color of products in which Capsanthin is used range from a deep red to a pale pinkish-yellow, depending on the concentrations used.
-Capsanthin, is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens (Indian red chillies), and is primarily used as a colouring and/or flavouring in food products.

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

SUBSTITUENTS of CAPSANTHIN:    
-Xanthophyll
-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 CAPSANTHIN:
Molecular Weight: 584.87
Appearance Form: solid
Color: red
Odor: No data available
Odor Threshold: No data available
pH: No data available
Melting point/freezing point: 165 - 169 °C
Initial boiling point and boiling range: No data available

Flash point: No data available
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Vapor pressure: No data available
Vapor density: No data available
Relative density: No data available
Water solubility: No data available

Partition coefficient: n-octanol/water: No data available
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity: No data available
Explosive properties: No data available
Oxidizing properties: No data available
Other safety information: No data available
Melting point: 181–182 °C (358–360 °F; 454–455 K)
Water Solubility: 0.00068 g/L    

logP: 8.2    
logP: 8.51    
logS: -5.9    
pKa (Strongest Acidic): 15.21    
pKa (Strongest Basic): -1.1    
Physiological Charge: 0    
Hydrogen Acceptor Count: 3    
Hydrogen Donor Count: 2    
Polar Surface Area: 57.53 Ų    
Rotatable Bond Count: 11    

Refractivity: 194.96 m³·mol⁻¹    
Polarizability: 73.9 ų    
Number of Rings: 2
Solubility:    
-Insoluble in water. 
-Soluble in oil. 
-Soluble in acetone.
-Soluble in ethanol, acetone (freely), chloroform (freely),oil, and methanol. 
-Insoluble in water.

Appearance: Dark Red oil liquid
Formulation :In natural oil form
Appearance :Oil
Physical State :Liquid
Storage :Store at room temperature
Boiling Point :726.64° C at 760 mmHg 
Density :1.01 g/mL 
Refractive Index: n20D 1.56 

Melting point:177-178℃
Alpha: Cd +36° (chloroform)
Boiling point: 581.82°C 
Density: 1.012
Refractive index: 1.4960 
Storage temp.: -20°C
pka: 14.85±0.60
λmaxλ: 467-471 nm Amax

FIRST AID MEASURES of CAPSANTHIN:
-Description of first-aid measures:
*If inhaled:
If breathed in, move person into fresh air. 
Remove to fresh air. 
Get immediate medical attention.

*In case of skin contact:
Wash off with soap and plenty of water.
Wash skin with soap and plenty of water for at least 15 minutes. 
Remove contaminated clothing. 
Wash clothing before reuse.

*In case of eye contact:
Flush eyes with water as a precaution.
Hold eyelids apart and flush eyes with plenty of water for at least 15 minutes. 

*If swallowed:
Rinse mouth with water.
Get medical attention. 
Do not induce vomiting unless directed to do so by medical personnel.

-Indication of any immediate medical attention and special treatment needed: 
No data available

ACCIDENTAL RELEASE MEASURES of CAPSANTHIN:
-Environmental precautions:
No special environmental precautions required.

-Methods and materials for containment and cleaning up:
Sweep up and shovel. 
Keep in suitable, closed containers for disposal.
Contain spill and collect, as appropriate.

FIRE FIGHTING MEASURES of CAPSANTHIN:
-Extinguishing media:
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
-Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
-Further information: No data available

EXPOSURE CONTROLS/PERSONAL PROTECTION of CAPSANTHIN:
-Control parameters:
Ingredients with workplace control parameters:
-Exposure controls:
--Appropriate engineering controls:
General industrial hygiene practice.

--Personal protective equipment:
*Eye/face protection:
Safety glasses.

*Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

*Respiratory protection:
Respiratory protection is not required.

*Control of environmental exposure:
No special environmental precautions required.

HANDLING and STORAGE of CAPSANTHIN:
-Conditions for safe storage, including any incompatibilities:
Store in cool place. 
Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature -20 °C

STABILITY and REACTIVITY of CAPSANTHIN:
-Reactivity: No data available
-Chemical stability:
Stable under recommended storage conditions.
-Possibility of hazardous reactions: No data available
-Conditions to avoid: No data available
Other decomposition products - No data available

SYNONYMS:
(3R,3′S,5′R)-3,3′-Dihydroxy-β,κ-caroten-6′-one
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
capsanthin, (3R,3'S,5'R,13-cis)-isomer
(3R,3's,5'r)-3,3'-Dihydroxy-beta,kappa-caroten-6'-one    
(3R,3'S,5'R)-3,3'-Dihydroxy-beta,kappa-caroten-6'-one    
3,3'-Dihydroxy-b,K-caroten-6'-one    
3,3'-Dihydroxy-b,k-caroten-6'-one    
3,3'-Dihydroxy-beta,kappa-caroten-6'one    
3,3'Dihydroxy-beta,kappa-caroten-6'one    
beta,kappa-Caroten-6'one, 3,3'dihydroxy-    
Capsanthin/capsorubin    
(3R,3'S,5'R)-3,3'-dihydroxy-β,κ-caroten-6'one
E 160c
C08584
Chili Red
Paprika Red
CAPSORUBINE
Yellow corn