Quick Search
CAS: 7235-40-7
MF: C40H56
MW: 536.89
EINECS: 230-636-6
E 160a is a β-carotene powdered preparation, carried on 30-50% maltodextrin, 40-60% gum acacia and 10-30% rapeseed oil.
A small amount of E 160a is used (DL-Alpha Tocopherol, Rosemary Extract) as well as some anti-caking agent (silicon dioxide).
E 160a can be used either as an additive (as an orange colour) or as a nutrient (to provide vitamin A).
E 160a gets its name from carrots, because it is the orange pigment naturally found in carrots.
E 160a are authorised as an additive and have the e-number ‘E 160a’.
E 160a is also known as ‘CI Food Orange 5’. This particular p-code is a diluted and stabilised preparation of ‘E 160a (i); E 160a (i) is the all trans isomer of beta-carotene together with minor amounts of other carotenoids.
E 160a is from synthetic source.
There are other types of E 160a, including E 160a (ii), which is the type that is derived from plant source (such as carrots/vegetable oils/grass/alfalfa/nettle), and E 160a (iii), which is the beta carotene that is derived by fermentation from Blakeslea trispora.
To check usage levels of E 160a as a food additive, check the food additives regulation (1333/2008) to see permitted usage levels and conditions of use based on the type of product.
E 160a are part of ‘Group II, Colours’.
E 160a is a red/orange-coloured fat-soluble terpenoid with antioxidant properties. Carotenoids are susceptible to oxidation and therefore vitamin E has been used in this preparation to make E 160a more stable.
E 160a appears yellow to orange in most applications (depending on the concentration) and is acceptable to use in a wide pH range of 2-14.
E 160a generally has good stability to heat (up to 100°C), light and acid.
E 160ais an organic compound which is a red-orange color obtained from carrot roots and also from some plants and fruits.
E 160a is used as a food additive to impart red orange color to food and beverages.
E 160a is prepared synthetically or obtained from natural sources.
Synthetic E 160a occurs as red crystals or as crystalline powder.
E 160a consists predominantly of all-trans-β-carotene, but may also contain minor amounts of cis-isomers and other carotenoids such as all-trans-retinal, beta-apo-12′-carotenal, and beta-apo-10′-carotenal.
E 160a is obtained by solvent extraction of carrots (Daucus carota), oil of palm fruit (Elaeis guinensis), sweet potato (Ipomoea batatas) and other edible plants with subsequent purification.
The main coloring principles are alpha-and β-Carotenes of which E 160a account for the major part.
E 160a is the liquid or solid portion of the mixture or the mixture itself obtained by the hexane extraction of edible carrots.
E 160a from Blakeslea trispora occurs as red, brownish-red, or purple-violet crystals or as crystalline powder, with the color varying depending on the solvents used and the crystallization conditions.
E 160a from Blakeslea trispora consists predominantly of all-trans-β-carotene, but may also contain minor amounts of cis-isomers and other carotenoids, of which γ-carotene is the most characteristic type.
E 160a is obtained by extraction from strains of the algae Dunaliella salina using the essential oil d-limonene.
E 160a is then prepared as a suspension in vegetable oil after removal of the essential oil.
The main coloring principles are trans- and cis–isomers of ß-carotene together with minor amounts of other carotenes including α-carotene, lutein, zeaxanthin and cryptoxanthin.
E 160a is an organic, strongly coloured red-orange pigment abundant in fungi, plants, and fruits.
E 160a is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons.
Among the carotenes, E 160a is distinguished by having beta-rings at both ends of the molecule.
E 160a is biosynthesized from geranylgeranyl pyrophosphate.
In some Mucoralean fungi, E 160a is a precursor to the synthesis of trisporic acid.
E 160a is the most common form of carotene in plants.
When used as a food coloring, E 160a has the E number E160a.: 119 The structure was deduced by Karrer et al. in 1930.
In nature, E 160a is a precursor (inactive form) to vitamin A via the action of beta-carotene 15,15'-monooxygenase.
Isolation of E 160a from fruits abundant in carotenoids is commonly done using column chromatography.
E 160a can also be extracted from the beta-carotene rich algae, Dunaliella salina.
The separation of E 160a from the mixture of other carotenoids is based on the polarity of a compound.
E 160a is a non-polar compound, so it is separated with a non-polar solvent such as hexane.
Being highly conjugated, E 160a is deeply colored, and as a hydrocarbon lacking functional groups, it is very lipophilic.
E 160a Chemical Properties
Melting point: 178-179 °C
Boiling point: 644.94°C (rough estimate)
Density: 1.000
Vapor pressure: 0.004Pa at 25℃
Refractive index: 1.5630 (estimate)
Fp: 103 °C
Storage temp.: -20°C
Solubility: hexane: 100 μg/mL, soluble
Form: powder
Color: red to purple
Water Solubility: Soluble in hexane, dimethyl sulfoxide, benzene, chloroform, cyclohexane. Insoluble in water.
Sensitive: Air & Light Sensitive
Merck: 14,1853
BRN: 1917416
Stability: Stable, but sensitive to air, heat and light.
Store at -20C under nitrogen.
Pyrophoric - may ignite spontaneously in air at room temperature.
InChIKey: OENHQHLEOONYIE-JLTXGRSLSA-N
LogP: 6.5 at 40℃ and pH6.5
CAS DataBase Reference: 7235-40-7(CAS DataBase Reference)
NIST Chemistry Reference: E 160a(7235-40-7)
EPA Substance Registry System: E 160a (7235-40-7)
Common Uses
E 160a can be used in a wide range of food and beverages including cider, malt beverages, water-based flavored drinks, margarines, cheeses, cake fillings, custards, yogurts, processed nuts, precooked pastas and noodles.
E 160a is a known antioxidant, and antioxidants are substances that may protect your cells from free radicals, which may play a role in heart disease, cancer and other diseases.
E 160a is a coloring agent used in margarine, cheese and pudding to produce the desired color, and is also used as an additive to yellow-orange color.
E 160a is also a precursor to carotenoids and vitamin A is beneficial in protecting the skin from dryness and peeling.
E 160a also slows cognitive decline and is beneficial to human health.
Health benefits
E 160a reduces the risk of cardiovascular health.(1)
E 160a helps to fight cancer and reduces the growth of cancer cells.(1)
E 160a is beneficial for brain and fights oxidative stress.(1)
E 160a helps to prevent breathing disorders like asthma and bronchitis.(1)
E 160a also helps to prevent diabetes.(1)
E 160a helps to strengthen immune system.(1)
Manufacturing Process
3.6 g (0.023 mol) of 3,8-dimethyl-3,5,7-decatrien-1,9-diyne were dissolved in 50 ml of absolute ether, and to the solution was added 0.05 mol of ethereal phenyl-lithium solution. The mixture was refluxed for 30 minutes.
Then a solution of 11 g (0.05 mol) of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-methyl- 2-buten-1-al in 100 ml of ether was added dropwise, and the reaction mixture was boiled for 2 hours.
The reaction mixture was then hydrolyzed with aqueous ammonium acetate solution, and the ethereal layer was separated, dried and concentrated.
The residue, i.e., 1,18-di(2,6,6-trimethyl-1- cyclohexen-1-yl)-3,7,12,16-tetramethyl-4,15-dihydroxy-2,7,9,11,16- octadecapentaen-5,13-diyne, was a resinous product (having 1.9 active hydrogen atoms and absorption maxima in the ultraviolet spectrum at 326 and 341 nm) which was used for the next step without any further purification.
The resin was dissolved in 200 ml of methylene chloride, 10 ml of glacial acetic acid were added to the solution, and the mixture was cooled to - 40°C in a carbon dioxide atmosphere, while stirring.
Then, 9 ml of aqueous hydrobromic acid (60%) were added in one portion, the mixture was stirred at -35°C for 1.5 minutes, and subsequently 200 ml of ice water were run into the mixture.
After further stirring the mixture for 2 hours at 0°C, the methylene chloride layer was separated, washed with water and sodium bicarbonate solution, dried with Na2SO4 andconcentrated in vacuo.
The residue, i.e., 11,12-11',12'-bisdehydro-betta-carotene, was a tough resin or a foamy solid (having no active hydrogen atoms and possessing absorption maxima in the ultraviolet spectrum at 334 and 408 nm).
E 160a can be purified by chromatography.
The crude product can also be used for the next step without any preliminary purification.
11.4 g of 11,12-11',12'-bisdehydro-β-carotene were dissolved in 100 ml of petroleum ether (boiling range 80° to100°C), and the solution was hydrogenated under normal conditions after the addition of 0.5 ml of quinoline and 5 g of a lead-poisoned palladium catalyst.
After the calculated amount of hydrogen had been absorbed, the catalyst was removed by filtration and the filtrate was extracted with dilute sulfuric acid to remove the quinoline. By concentrating the solution in the usual manner there was obtained 11,12- 11',12'-di-cis-carotene.
The product was purified by recrystallization from benzene-alcohol.
The purified product melts at 154°C; absorption maxima in the ultraviolet spectrum at 276, 334, 338, 401 and 405 nm.
The isomerization was effected by heating the product for 10 hours at 90 to 100°C in high-boiling petroleum ether in a carbon dioxide atmosphere.
The resulting and carotene melted at 180°C; ultraviolet absorption maxima at 452 and 480 nm.
Preparation of the intermediates for the above chemical synthesis are also described in US. Patent 2,917,539.
The other patents cited below describe a fermentation route.
US Patent 2,848,508 describes preparation from carrots.
Synonyms
beta-carotene
7235-40-7
beta Carotene
beta,beta-Carotene
Betacarotene
Solatene
Provitamin A
Carotaben
Provatene
all-trans-beta-Carotene
Serlabo
Food orange 5
KPMK
Lucaratin
BetaVit
Natural Yellow 26
Karotin
Provatenol
beta-Karotin
b-Carotene
b,b-Carotene
.beta.-Carotene
C.I. Food Orange 5
.beta.,.beta.-Carotene
Zlut prirodni 26
CI Food Orange 5
Carotene,beta
beta-Carotin
beta -carotene
beta;-Carotene
CI 40800
CI 75130
.beta. Carotene
all-trans-.beta.-Carotene
Lucarotin 30sun
C.I. 75130
NSC 62794
Beta, beta-carotene
Betacarotene [INN]
(all-E)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethylcyclohexene)
1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene
116-32-5
Ins-160a(iii)
Ins no.160a(iii)
Caroten base 35468
Rovimix .beta.-carotene
E-160a(iii)
MLS001066383
01YAE03M7J
2,2'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(1,3,3-trimethylcyclohex-1-ene)
CHEBI:17579
NSC62794
Betacarotene (INN)
NSC-62794
1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethylcyclohexene), (all E)-
NCGC00096081-01
SMR000112037
C.I.-40800
Solatene (caps)
Karotin [Czech]
Cyclohexene, 1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethyl-, (all-E)-
.beta.-Carotene, all-trans-
Betacarotenum [Latin]
beta carotene [USAN]
Betacaroteno
Betacaroteno [Spanish]
Betacarotenum
MFCD00001556
beta-Carotene, all-trans-
Betacarotenum [INN-Latin]
Betacaroteno [INN-Spanish]
Zlut prirodni 26 [Czech]
1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene)
trans-beta-Carotene
CCRIS 3245
HSDB 3264
Diet,beta-carotene supplementation
E160A
SR-01000763803
EINECS 230-636-6
Beta carotene [USAN:USP]
UNII-01YAE03M7J
Lucarotin
Lurotin
beta-Carotine
all-E-b-Carotene
Rovimix b-carotene
Carotene, .beta.
Solatene (TN)
Cyclohexene, 1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-, (all-E)-
I(2)-Carotene
Carotene Base 80S
all-trans-b-Carotene
Beta Carotene Natural
beta Carotene (USP)
trans-.beta.-Carotene
Carotene, Provitamin A
all trans beta-Carotene
b-Carotene - 30%
all-E-.beta.-Carotene
all-epsilon-beta-Carotene
DSSTox_CID_253
Spectrum5_000505
.beta., .beta.-Carotene
bmse000832
EC 230-636-6
C40H56 (beta-carotene)
(9Z,13Z)-beta-Carotene
BETA CAROTENE [DSC]
BETA-CAROTENE [FCC]
CHEMBL1293
DSSTox_RID_75466
BIDD:PXR0110
DSSTox_GSID_20253
BETA CAROTENE [HSDB]
BETA-CAROTENE [INCI]
BETACAROTENE [MART.]
BSPBio_003404
BETA CAROTENE [VANDF]
BETACAROTENE [WHO-DD]
CAROTENE,BETA [VANDF]
.BETA.-CAROTENE [MI]
BETA CAROTENE [USP-RS]
DTXSID3020253
BDBM54988
cid_5280489
HMS501A12
.beta.,.beta.-Carotene, neo B
BETACAROTENE [EP IMPURITY]
CI 40800 [INCI]
CI 75130 [INCI]
HMS2091M17
Pharmakon1600-01500143
BETACAROTENE [EP MONOGRAPH]
BETA CAROTENE [ORANGE BOOK]
HY-N0411
ZINC6845076
beta-Carotene, >=97.0% (UV)
Tox21_111557
CCG-36062
LMPR01070001
NSC755910
s1767
BETA CAROTENE [USP MONOGRAPH]
AKOS015896682
AC-1869
DB06755
NSC-755910
SDCCGMLS-0066579.P001
IDI1_000330
NCGC00096081-02
AS-13354
XC175229
CAS-7235-40-7
SBI-0051295.P003
SW220035-1
C02094
D03101
AB00051925_06
AB00051925_07
beta-Carotene, Vetec(TM) reagent grade, >=93%
EN300-21680271
Q306135
Q-200706
SR-01000763803-2
SR-01000763803-3
SR-01000763803-4
BETA-CAROTENE (CONSTITUENT OF SPIRULINA) [DSC]
beta-Carotene, Type I, synthetic, >=93% (UV), powder
89648336-F9B2-44A0-9BF8-62E73369CB9B
Beta Carotene, United States Pharmacopeia (USP) Reference Standard
beta-Carotene, Type II, synthetic, >=95% (HPLC), crystalline
BETA-CAROTENE (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]
beta-Carotene, Pharmaceutical Secondary Standard; Certified Reference Material
Cyclohexane,1,1'-(3,7,12,16-tetramethyl-1,18-octadecanediyl)bis[2,2,6-trimethyl-
(all-E)-1,1'-(3,7,12,16-Tetramethyl-1,3,5, 7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6, 6-trimethylcyclohexene]
(all-E)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis
(all-E)-1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-Cyclohexene
1,18-Bis(2,6,6-trimethyl-1-cyclohexenyl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonene
1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
