BIXIN

Bixin is used in lipsticks, creams, and other formulations requiring natural coloring.
Bixin may be used as a coloring agent in capsules and coatings.
Bixin is also used in traditional food systems in Latin America and tropical regions where annatto is cultivated.

CAS Number: 476-66-4
EC Number: 207-508-8
MDL Number: MFCD00016545
E Number: E160b(i) 
E160b(i) = bixin (fat-soluble)
Molecular Formula: C₂₅H₃₀O₄
Molecular Weight: 394.51 g/mol

SYNONYMS:
Bixin, Annatto pigment, Norbixin methyl ester (related form), E160b(i), CI Natural Orange 4, Bixa orellana extract, Rocou dye (annatto-derived), Lipid-soluble annatto pigment, IUPAC name: (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-Methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid, cis-Bixin; α-Bixin; 9-cis-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester, Bixin, 6983-79-5, (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid, DTXSID1024629, Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioate, 9L7T4VB66G, Annatto (E 160b), E160b, CHEBI:3136, DTXCID304535, 2,4,6,8,10,12,14,16,18-Eicosanonaenedioic acid, 4,8,13,17-tetramethyl-, monomethyl ester, (2E,4Z,6E,8E,10E,12E,14E,16E,18E)-, RefChem:29838, 230-248-7, cis-Bixin, 20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid, Isobixin, Stable bixin, 6'-methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioate, 6'-methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate, C25H30O4, alpha-Bixin, EINECS 230-248-7, UNII-9L7T4VB66G, CCRIS 9384, a-Bixin, (9-cis)-6,6'-diapo-?,?-carotenedioic acid 6-methyl ester; a-Bixin; Bixinol, BIXINS CIS-FORM, .ALPHA.-BIXIN, BIXIN [MART.], BIXINS CIS-FORM [MI], orb1710247, orb3140792, SCHEMBL9939959, CHEMBL1172615, 6-Methyl hydrogen (9Z)-6,6'-diapocarotene-6,6'-dioate, HMS6018A15, Bixin, >=95.0% (HPLC), HY-N6884, Tox21_303095, MSK157564, AKOS040732608, FB31050, NCGC00257045-01, MS-26633, CAS-6983-79-5, CS-0100483, C08582, T10554, Q424572, 6,6'-DIAPO-.PSI.,.PSI.-CAROTENEDIOIC ACID, 6-METHYL ESTER, 9-CIS-, (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxo-icosa-2,4,6,8,10,12,14,16,18-nonaenoic acid, 2,4,6,8,10,12,14,16,18-EICOSANONAENEDIOIC ACID, 4,8,13,17-TETRAMETHYL-, 1-METHYL ESTER, (2E,4Z,6E,8E,10E,12E,14E,16E,18E)-, 6-Methyl hydrogen (9Z)-6,6′-diapocarotene-6,6’-dioate, 9-cis-6,6′-Diapo-ψ,ψ-carotenedioic acid 6-methyl ester, Natural orange 4, bixin, cis-bixin, trans-bixin, annatto red, annatto pigment (oil-soluble form), bixa orellana extract (oil-soluble fraction), achiote oil pigment, CI Natural Orange 4, CI 75120, annatto extract oil soluble, E160b(i), bixin pigment, orlean pigment, lipstick tree seed oil pigment, annatto carotenoid (bixin form)

Bixin is a carotenoic acid that is found in Bixin Orellana and Apis cerana.
Bixin functions as an insulin-sensitizing drug, an antioxidant, a biological pigment, and an anti-inflammatory agent.
Additionally, bixin is a dicarboxylic acid monoester and a methyl ester that is known as the second widely used natural pigment in the world.

Research has been conducted which shows serious interest in the biosynthetic pathway and application of bixin.
Bixin is an apocarotenoid and is used as a natural food coloring.
E160b(i), known as bixin, is a naturally occurring carotenoid pigment extracted from the seeds of the annatto plant (Bixa orellana).

Bixin is one of the primary components responsible for the yellow to reddish-orange color of annatto extracts.
Bixin is fat-soluble and widely used as a natural food colorant, especially in dairy products, snacks, and processed foods.
Bixin is valued for being plant-derived and relatively stable compared to other natural pigments.

Bixin is one of two main annatto pigments; the other is norbixin (water-soluble form).
Bixin can be converted to norbixin through saponification (alkaline hydrolysis), which increases its water solubility.
Bixin's stability depends strongly on processing conditions, especially exposure to light and oxygen.

Compared to synthetic dyes, bixin offers a natural alternative but with slightly lower stability in harsh processing conditions.
Bixin is an apocarotenoid found in the seeds of the achiote tree (Bixa orellana) from which it derives its name.
Bixin is commonly extracted from the seeds to form annatto, a natural food coloring, containing about 5% pigments, of which 70–80% are bixin.

Bixin is the original form of annatto that is extracted from the seed coating and is naturally oil soluble.
One method to extract bixin from the seed coat is using hot vegetable oil.
However, bixin is only soluble in vegetable oil at low percentage rates.

You can create stronger products by using bixin suspensions.
This is done through repeat extractions of annatto seeds yielding bixin concentrations of 4% or greater.
Oil soluble bixin is a yellow color, whereas suspensions of bixin are a deep, vivid red orange.

Bixin is an organic compound that serves as a natural antioxidant and colorant, which is derived from the seeds of the annatto tree (Bixa orellana).
The mode of action of bixin involves its ability to scavenge free radicals, thereby preventing oxidative stress and lipid peroxidation.
Its chemical structure allows Bixin to efficiently stabilize reactive oxygen species, making it highly effective in preserving the integrity of biological and chemical systems.

Bixin is an apocarotenoid found in the roucou plant (Bixa orenalla), from which it takes its name.
Bixin is listed as a food additive under number E160b (i).
Bixin is a colorant.

Roucou seeds contain around 5% pigment, 70-80% of which is bixin.
Norbixin is a bixin-like compound that can be obtained from bixin.
The methyl ester end of bixin is hydrolyzed in an alkaline medium to form a carboxylic acid.

Norbixin from red mulberry is also a food colorant, under the number E160b(ii).
The roucouyer is a species of tree or shrub native to the tropical regions of South America.
Its pink flowers produce spiny red fruits filled with red seeds.

The seed shells produce a dye called roucou.
The seeds are harvested and dried to extract the wax surrounding the carotenoid-rich seeds.
Bixin is an apocarotenoid found in annatto, a natural food coloring obtained from the seeds of the achiote tree (Bixa orellana).

Annatto seeds contain about 5% pigments, which consist of 70-80% bixin.
Bixin is chemically unstable when isolated and converts via isomerization into trans-bixin (β-bixin), the double-bond isomer.

Bixin is soluble in fats and alcohols but insoluble in water.
Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative.

USES and APPLICATIONS of BIXIN:
Key Applications of Bixin: Natural cheese coloring (including Cheddar and Red Leicester), processed cheese, snacks, fats, oils, butter, and margarine.
Benefit: Bixin provides excellent light stability and a natural, “clean label” alternative to synthetic dyes.
Bixin is widely used in the food and related industries.

In the food industry, Bixin is used as a natural colorant in cheese (especially cheddar), butter, margarine, baked goods, snacks, and processed foods.
In dairy products, Bixin is one of the most important natural colorants due to its stability in fat-rich systems.
In cosmetics, Bixin is used in lipsticks, creams, and other formulations requiring natural coloring.

In pharmaceutical applications, Bixin may be used as a coloring agent in capsules and coatings.
Bixin is also used in traditional food systems in Latin America and tropical regions where annatto is cultivated.
Bixin is a commonly used natural color in the food industry because it is an economical option for yellow to red-orange hues depending on the application and dosage rate.

Since bixin is oil-soluble, it is mostly used in oil-based food applications like process cheese, cheese sauces, and dairy spreads.
Bixin is also a popular choice in the snack food industry where it may be applied to oil-based slurries used to season extruded snacks.
In the realm of its applications, bixin is extensively utilized in the food industry as a natural colorant, imparting a reddish-yellow hue to various products.

Beyond its role in food technology, bixin's antioxidative properties make it valuable in cosmetics and pharmaceuticals, where it helps to maintain the stability and efficacy of formulations.

Furthermore, recent studies have explored Bixin's potential implications in biomedicine, investigating antioxidative roles within cellular systems that may mitigate certain pathophysiological conditions.
Ongoing research continues to elucidate its multifaceted functionalities and applications across diverse scientific domains.

-The Ideal Solution for Oil-Based Applications of Bixin:
The primary pigment found in annatto seeds is Bixin.
Due to its fat-soluble nature, Bixin is the industry standard for achieving consistent, vibrant orange and yellow hues in oil-based products.

CHEMICAL PROPERTIES of BIXIN:
Bixin is unstable.
Bixin isomerizes into trans-bixin (β-bixin), the double-bond isomer.
Bixin is soluble in fats and alcohols but insoluble in water.

Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative.
Bixin is a carotenoic acid that is the 6'-monomethyl ester of 9'-cis-6,6'-diapocarotene-6,6'-dioic acid.
Bixin has a role as an antioxidant, a biological pigment, an insulin-sensitizing drug, an anti-inflammatory agent, an apoptosis inducer and a food colouring.

Bixin is a methyl ester, a carotenoic acid and a dicarboxylic acid monoester.
Bixin has been reported in Bixa orellana and Apis cerana with data available.

BENEFITS of BIXIN:
Bixin offers several advantages:
*Natural plant-derived colorant
*Strong orange-red coloration
*Good stability in lipid systems
*High coloring efficiency at low doses
*Consumer-friendly “clean label” ingredient
*Mild antioxidant properties

PHYSICAL AND CHEMICAL PROPERTIES of BIXIN:
Bixin appears as an orange-red crystalline solid or powder.
Bixin is odorless and has a mild characteristic plant-derived odor in crude extracts.
Bixin is insoluble in water but soluble in oils, fats, and organic solvents such as acetone, chloroform, and ethanol.

This lipophilic nature makes Bixin suitable for fat-based food systems.
Bixin has a melting point in the range of 180–185°C, where decomposition may also begin depending on purity.
Chemically, bixin is a carotenoid monomethyl ester containing a long conjugated polyene chain with carboxylic and ester functional groups.

This structure is responsible for Bixin's strong coloration and moderate antioxidant properties.
Bixin is sensitive to light, oxygen, and heat, which can cause isomerization and degradation, leading to color fading over time.
Bixin is non-ionic and highly lipophilic.

CHARACTERISTICS of BIXIN:
Bixin is characterized by:
*Orange to reddish-orange coloration
*Lipophilic (fat-soluble) pigment
*Carotenoid ester structure
*Conjugated polyene chain
*Moderate antioxidant activity
*Sensitivity to oxidation and light
*Insolubility in water
*Stability in oil-based systems

PHYSICAL and CHEMICAL PROPERTIES of BIXIN:
Appearance: Orange-red crystalline powder
Color: Yellow-orange to reddish-orange
Odor: Mild plant-like odor
Taste: Neutral
Physical State: Solid
Solubility in Water: Insoluble
Solubility in Organic Solvents: Soluble in oils, fats, acetone, ethanol, chloroform

Molecular Nature: Carotenoid ester (monomethyl ester)
Chemical Structure: Long conjugated polyene chain with ester and carboxyl groups
Polarity: Non-polar (lipophilic)
Ionic Character: Non-ionic
Melting Point: ~180–185°C (with decomposition)
Boiling Point: Not defined (decomposes before boiling)

Thermal Stability: Moderate; sensitive to high heat
Light Stability: Sensitive to photodegradation
Oxidation Stability: Sensitive to oxygen exposure
Reactivity: Reactive due to conjugated double bonds
Volatility: Non-volatile
Hygroscopicity: Low
Color Strength: High in fat-based systems
Antioxidant Activity: Moderate

Chemical formula: C25H30O4
Molar mass: 394.511 g·mol−1
Appearance: Orange crystals
Melting point: 198 °C (cis-isomer)
217 °C (trans-isomer)
Solubility in water: Insoluble
Molecular Weight: 394.5 g/mol
XLogP3-AA: 7.5

Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 11
Exact Mass: 394.21440943 Da
Monoisotopic Mass: 394.21440943 Da
Topological Polar Surface Area: 63.6 Ų
Heavy Atom Count: 29

Formal Charge: 0
Complexity: 823
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 9
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1

Compound Is Canonicalized: Yes
CAS#: 6983-79-5
Chemical Formula: C25H30O4
Exact Mass: 394.2144
Molecular Weight: 394.51
Elemental Analysis: C, 76.11; H, 7.67; O, 16.22
Synonym: Bixin
IUPAC/Chemical name: (2e,4e,6e,8e,10e,12e,14e,16z,18e)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid

InChI key: rafgelqlhmbrhd-slezcnmesa-n
InChI code: inchi=1s/c25h30o4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19h,1-5h3,(h,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
SMILES code: coc(/c=c/c(c)=cc=cc(c)=cc=cc=c(c=cc=c(c=cc(o)=o)c)c)=o
Appearance: solid
Storage condition: dry, dark and at 0 - 4 c for short term (days to weeks) or -20 c for long term (months to years).
Solubility: to be determined
HS tariff code: 2934.99.9001

Empirical formula (Hill notation): c25h30o4
CAS number: 6983-79-5
Molecular weight: 394.50
PubChem substance id: 329748187
UNSPSC code: 12352202
NACRES: na.32
EC number: 230-248-7
Colour index number: 75120

Physical state: solid
Color: red
Odor: no data available
Melting point/freezing point: 190 - 198 °c
Initial boiling point and boiling range: no data available
Flammability (solid, gas): no data available
Upper/lower flammability or explosive limits: no data available
Flash point: not applicable

Autoignition temperature: no data available
Decomposition temperature: no data available
pH: no data available
Viscosity, kinematic: no data available
Viscosity, dynamic: no data available
Water solubility: no data available
Partition coefficient: n-octanol/water: no data available
Vapor pressure: no data available
Density: no data available

Relative density: no data available
Relative vapor density: no data available
Particle characteristics: no data available
Explosive properties: not classified as explosive
Oxidizing properties: none
Other safety information: no data available
Mono-carboxy carotenoid
Appearance: Dark brown
Insoluble in water and acid

Partially soluble in oil
Soluble in alkali
Appearance: Orange-red to reddish crystalline powder or resinous solid
Odor: Mild, characteristic plant-derived odor (very weak in purified form)
Taste: Slightly bitter or neutral (at food-grade levels generally imperceptible)
Color range: Yellow-orange → orange-red → deep red depending on concentration
Physical state: Solid (crystalline or amorphous pigment extract)
Solubility in water: Insoluble
Solubility in oils/fats: Highly soluble (lipophilic pigment)

Solubility in organic solvents: Soluble in non-polar and moderately polar organic solvents (e.g., acetone, chloroform, ethanol to some extent)
Stability to light: Low to moderate (light-sensitive, gradual fading occurs)
Stability to heat: Moderate (more stable in fats than in aqueous systems)
Stability to oxygen: Moderate to low (oxidative degradation over time)
Density: Not fixed (depends on crystalline form and purity)
Melting point: ~200–210 °C (often with decomposition rather than clean melting)
Volatility: Non-volatile

Chemical nature: Lipophilic apocarotenoid methyl ester
Molecular structure type: Long conjugated polyene chain (responsible for strong coloration)
Functional groups:
Methyl ester group (-COOCH₃)
Conjugated double-bond system
Molecular behavior: Non-polar carotenoid with high fat affinity
Acidity/basicity: Neutral (ester form; not acidic like norbixin)
Isomerism: Exists mainly as cis and trans isomers (cis-bixin is common in natural extracts)
Reactivity:

Sensitive to oxidation
Sensitive to light-induced isomerization
Thermal behavior: Stable under moderate heating in fats but degrades at high temperature
Hydrolysis behavior: Converts to norbixin under alkaline conditions (loss of methyl ester group)
Redox sensitivity: Easily oxidized leading to color loss or degradation products
Spectral property: Strong absorption in visible range due to extended conjugation (responsible for red-orange color)
Chemical stability: Better in lipid environments than in aqueous systems
Degradation pathway: Oxidation, isomerization, and thermal breakdown of polyene chain

FIRST AID MEASURES of BIXIN:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of BIXIN:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of BIXIN:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of BIXIN:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of BIXIN:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of BIXIN:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available