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1107-26-2

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  • 2,4,6,8,10,12,14,16-Heptadecaoctaenal,2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(2E,4E,6E,8E,10E,12E,14E,16E)-

    Cas No: 1107-26-2

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1107-26-2 Usage

Content analysis

Sample solution A: Accurately weigh about 40 mg of the sample, transfer it into a 100 ml volumetric flask, dissolve it in 10 ml of acid-free chloroform, make up to volume with cyclohexane and mix well. Pipette 2ml of this solution into a 50ml volumetric flask, dilute to volume with cyclohexane and mix well. Pipette 5ml of sample solution A into a 50ml volumetric flask with sample solution B, dilute to volume with cyclohexane and mix well. Determination step Use a suitable spectrophotometer to measure the absorbance of sample solution B in a 1CiTI absorption cell at the maximum absorption wavelength of about 460nm, and use cyclohexane as a blank test solution. Calculate the content (in mg) of this product (C30H40O) in the sample according to the formula 25000A/264, where A is the absorbance of the solution, and 264 is the absorbance coefficient of pure β-apocarcinaldehyde.

Description

trans-β-Apo-8′-carotenal is a dark purple crystal or crystalline fine powder with metallic luster. It is one of the oxidation products of carotenoids contained in citrus. It is insoluble in water and can be dispersed in hot water. It is easily soluble in chloroform, insoluble in ethanol, and slightly soluble in vegetable oil and acetone. Industrial products soluble in oils or organic solvents, with stable performance.

Chemical Properties

Fine crystalline powder with dark metal- lic sheen or violet crystals.Sol in chlo- roform; sltly sol in acetone; insol in water.

Uses

Different sources of media describe the Uses of 1107-26-2 differently. You can refer to the following data:
1. β-apo-8 -carotenal is used to color juices, fruit drinks, soups, jams, jellies, and gelatin.
2. β-Apo-8'-carotenal is an antioxidant β-carotene (C184250) derivative found in Cucumis melo melons and traditional Portuguese fruits and vegetables. Studies have shown that β-Apo-8'-carotenal decreased the in vivo AFB1-induced DNA SSB and the binding of AFB1 to liver DNA and increased in vitro AFB1 metabolism to aflatoxin M1, a less genotoxic metabolite.
3. Beta-Apo-8'-Carotenal is a colorant that is a carotenoid producing a light to dark orange hue. It has fair light stability, poor oxidation stability, and good ph stability. It is insoluble in water but is available in water-dispersible, oil-dispersible, and oil-soluble forms. It has vitamin a activity. It is used in cheese and cheese sauces, and dressings. The maximum usage level is 33 ppm. Related colorants are beta-carotene and canthaxanthin.

Definition

ChEBI: An apo carotenoid triterpenoid compound arising from oxidative degradation of the beta,beta-carotene skeleton at the 8'-position.

General Description

trans-β-Apo-8′-carotenal is a linear aldehydic carotenoid. It is naturally found in oranges, spinach, grass, tangerines and marigolds and thus, it is directly absorbed from the diet.

Biochem/physiol Actions

trans-β-Apo-8′-carotenal is commercially available as a food colorant.

Safety Profile

When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Recrystallise β-apo-8'-carotenal from CHCl3/EtOH mixture or n-hexane. [Bobrowski & Das J Org Chem 91 1210 1987, Beilstein 7 III 2622, 7 IV 1782.]

Properties and Applications

orange to yellow light red.

Check Digit Verification of cas no

The CAS Registry Mumber 1107-26-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,0 and 7 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1107-26:
(6*1)+(5*1)+(4*0)+(3*7)+(2*2)+(1*6)=42
42 % 10 = 2
So 1107-26-2 is a valid CAS Registry Number.

1107-26-2 Well-known Company Product Price

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  • (1040854)  Apocarotenal  United States Pharmacopeia (USP) Reference Standard

  • 1107-26-2

  • 1040854-3X50MG

  • 4,662.45CNY

  • Detail

1107-26-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 8'-apo-β,ψ-caroten-8'-al

1.2 Other means of identification

Product number -
Other names (2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food Additives: COLOUR
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1107-26-2 SDS

1107-26-2Synthetic route

crocetindial
502-70-5

crocetindial

C28H32ClP

C28H32ClP

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Stage #1: C28H32ClP With sodium methylate In methanol at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere;
Stage #2: crocetindial In methanol at 20℃; for 4h; Time; Wittig Olefination; Inert atmosphere;
38%
beta-carotene
7235-40-7

beta-carotene

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
With potassium permanganate; water; benzene at 20℃; Reagens 4: Na2CO3;
(2E,4E,6E)-8,8-dimethoxy-3,7-dimethyl-octa-2,4,6-trienal
5095-50-1

(2E,4E,6E)-8,8-dimethoxy-3,7-dimethyl-octa-2,4,6-trienal

Retinyltriphenylphosphonium Chloride
3991-53-5

Retinyltriphenylphosphonium Chloride

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
With sodium methylate
1-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraene-1-sulfonyl]-4-phenoxy-benzene
56859-10-0

1-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraene-1-sulfonyl]-4-phenoxy-benzene

(2E,4E,6E)-8-bromo-2,6-dimethyl-octa-2,4,6-trienal
56859-12-2

(2E,4E,6E)-8-bromo-2,6-dimethyl-octa-2,4,6-trienal

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
With sodium ethanolate In ethanol; N,N-dimethyl-formamide
lycopene
502-65-8

lycopene

8'-Apo-β-caroten-8'-al radical cation

8'-Apo-β-caroten-8'-al radical cation

A

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

B

lycopene radical cation

lycopene radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
zeaxanthin
144-68-3

zeaxanthin

8'-Apo-β-caroten-8'-al radical cation

8'-Apo-β-caroten-8'-al radical cation

A

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

B

zeaxanthin radical cation

zeaxanthin radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
beta-carotene
7235-40-7

beta-carotene

8'-Apo-β-caroten-8'-al radical cation

8'-Apo-β-caroten-8'-al radical cation

A

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

B

all-trans β-carotene radical cation

all-trans β-carotene radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
beta-carotene
7235-40-7

beta-carotene

A

(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-Tetramethyl-17-(2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-heptadeca-2,4,6,8,10,12,14,16-octaenal

(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-Tetramethyl-17-(2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-heptadeca-2,4,6,8,10,12,14,16-octaenal

B

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

C

15-cis-β-carotene
19361-58-1

15-cis-β-carotene

D

5,6-epoxy-5,6-dihydro-β,β-carotene
1923-89-3

5,6-epoxy-5,6-dihydro-β,β-carotene

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; (carbonyl)(5,10,15,20-tetramesitylporphyrinato)ruthenium(II) In benzene at 20℃; for 6h; Product distribution; Further Variations:; reaction time;
15,15'-didehydro-8'-apo-β-caroten-8'-al
10464-96-7

15,15'-didehydro-8'-apo-β-caroten-8'-al

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lindlar-catalyst; quinoline; toluene / Hydrogenation
2: petroleum ether
View Scheme
15,15'-didehydro-10'-apo-β-caroten-10'-al-diethylacetal
103400-22-2

15,15'-didehydro-10'-apo-β-caroten-10'-al-diethylacetal

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene; ZnCl2; ethyl acetate / Erwaermen des Reaktionsprodukts mit Natriumacetat und wss. Essigsaeure
2: Lindlar-catalyst; quinoline; toluene / Hydrogenation
3: petroleum ether
View Scheme
8-acetoxy-2,6-dimethyl-octa-2,4,6-trien-1-al
3950-23-0

8-acetoxy-2,6-dimethyl-octa-2,4,6-trien-1-al

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) TsOH, MeOH, (ii) aq. NaOH, (iii) MnO2
2: NaOMe
View Scheme
Retinol acetate
127-47-9

Retinol acetate

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. propan-2-ol
2: NaOEt / ethanol; dimethylformamide
View Scheme
RETINOL
68-26-8

RETINOL

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / ethanol
2: NaOMe
View Scheme
beta-carotene
7235-40-7

beta-carotene

A

(E)-β-ionone
79-77-6

(E)-β-ionone

B

4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal
640-49-3

4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal

C

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

D

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

E

5,6-epoxy-trans-β-ionone
36340-49-5

5,6-epoxy-trans-β-ionone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; μ-carbido-bis[(5,10,15,20-tetraphenyl-21H,23H-porphyrinato)iron(IV)] In benzene at 24.84℃; Kinetics; Reagent/catalyst;
With tert.-butylhydroperoxide; μ-carbido bis(2,3,7,8,12,13,17,18-octapropyl-5,10,15,20-tetraazaporphinato)iron(IV) In benzene at 25℃; Kinetics; Reagent/catalyst;
all-trans-β-apo-8'-Carotenol
6541-41-9

all-trans-β-apo-8'-Carotenol

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Conditions
ConditionsYield
With manganese(IV) oxide In 1,2-dichloro-ethane at 25 - 30℃; for 10h; Solvent; Temperature; Inert atmosphere;2.58 g
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

4-methoxycarbonylbenzyltriphenylphosphonium bromide
1253-46-9

4-methoxycarbonylbenzyltriphenylphosphonium bromide

(7'E)-7'-<(4-methoxycarbonyl)phenyl>-7'-apo-β-carotene
90652-11-2

(7'E)-7'-<(4-methoxycarbonyl)phenyl>-7'-apo-β-carotene

Conditions
ConditionsYield
With sodium methylate In toluene for 1h; Heating;94%
With sodium methylate In toluene for 7h; Heating;62%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

Ethyl 6'-apo-β-caroten-6'-oate
128184-28-1

Ethyl 6'-apo-β-caroten-6'-oate

Conditions
ConditionsYield
With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h;94%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

malononitrile
109-77-3

malononitrile

all-trans-7',7'-dicyano-7'-apo-β-caroten
128184-27-0

all-trans-7',7'-dicyano-7'-apo-β-caroten

Conditions
ConditionsYield
With ammonium carbonate; propionic acid In benzene at 70℃; Knoevenagel condensation; Inert atmosphere;85%
With piperidine In benzene for 3.2h;57%
With triethylamine15%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

pyridin-4-ylacetonitrile hydrochloride

pyridin-4-ylacetonitrile hydrochloride

all-trans-7'-cyano-7'-pyridyl-7'-apo-β-carotene
1263469-92-6

all-trans-7'-cyano-7'-pyridyl-7'-apo-β-carotene

Conditions
ConditionsYield
Stage #1: trans-β-apo-8'-carotenal; pyridin-4-ylacetonitrile hydrochloride With ammonium carbonate; propionic acid In benzene at 70℃; Knoevenagel condensation; Inert atmosphere;
Stage #2: acid-base-catalyzed Knoevenagel condensation;
82%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

(+/-)-Essigsaeure-<(2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid
86530-42-9

(+/-)-Essigsaeure-<(2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid

(+/-)-2'-O-Acetylaleuriaxanthin
51276-30-3, 86561-91-3, 86630-80-0

(+/-)-2'-O-Acetylaleuriaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane 1.) r.t., 20 h; 2.) reflux, 45 min;75%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

pyrrolidinium perchlorate
22401-44-1

pyrrolidinium perchlorate

(all trans)-1-<2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10,12,14,16-heptadecaoctaenylidene>pyrrolidinium perchlorate

(all trans)-1-<2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10,12,14,16-heptadecaoctaenylidene>pyrrolidinium perchlorate

Conditions
ConditionsYield
With 4 A molecular sieve In ethanol; dichloromethane for 48h; Ambient temperature;70%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

5-amino-25,27-dihydroxy-26,28-dimethoxycalix<4>arene

5-amino-25,27-dihydroxy-26,28-dimethoxycalix<4>arene

C60H67NO4

C60H67NO4

Conditions
ConditionsYield
In toluene for 24h; Heating;63%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

(-)-Essigsaeure-<(6S,2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid

(-)-Essigsaeure-<(6S,2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid

(2'S)-2'-O-Acetylaleuriaxanthin

(2'S)-2'-O-Acetylaleuriaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane 1.) r.t., 20 h; 2.) reflux, 45 min;62%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

(+)-Essigsaeure-<(6R,2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid

(+)-Essigsaeure-<(6R,2E)-6-acetoxy-3,7-dimethyl-2,7-octadien-1-yl>triphenylphosphonium-bromid

(2'R)-2'-O-Acetylaleuriaxanthin

(2'R)-2'-O-Acetylaleuriaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane 1.) r.t., 20 h; 2.) reflux, 45 min;62%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

(6S)-1-bromo-3-methyl-6,7-O-isopropylidene-2,4-heptadiene-6,7-diol
84693-16-3

(6S)-1-bromo-3-methyl-6,7-O-isopropylidene-2,4-heptadiene-6,7-diol

(6S)-6,7-dihydroxy-O-isopropylidene-3-methyl-2,4-heptadienyl triphenylphosphonium bromide

(6S)-6,7-dihydroxy-O-isopropylidene-3-methyl-2,4-heptadienyl triphenylphosphonium bromide

Conditions
ConditionsYield
In diethyl ether for 84h; Ambient temperature;59%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

C28H58O2PSi(1+)*Cl(1-)

C28H58O2PSi(1+)*Cl(1-)

(2'R)-3',4'-didehydro-1',2'-dihydro-1',2'-dihydroxy-α-psi-carotene

(2'R)-3',4'-didehydro-1',2'-dihydro-1',2'-dihydroxy-α-psi-carotene

Conditions
ConditionsYield
Stage #1: trans-β-apo-8'-carotenal; C28H58O2PSi(1+)*Cl(1-) With sodium methylate In methanol; dichloromethane at 20℃; for 0.333333h; Wittig Olefination; Inert atmosphere;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;
54%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

pyrrolidinium hydroiodide
45361-12-4

pyrrolidinium hydroiodide

(all trans)-1-<2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10,12,14,16-heptadecaoctaenylidene>pyrrolidinium iodide

(all trans)-1-<2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10,12,14,16-heptadecaoctaenylidene>pyrrolidinium iodide

Conditions
ConditionsYield
With 4 A molecular sieve In ethanol; dichloromethane for 48h; Ambient temperature;53%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

dansyl hydrazine
33008-06-9

dansyl hydrazine

dansyl-carotenal

dansyl-carotenal

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethanol for 3h;47%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

2,4,6-tri(β-apo-9'-carotenyl)-1,3,5-trithiane

2,4,6-tri(β-apo-9'-carotenyl)-1,3,5-trithiane

Conditions
ConditionsYield
With Lawessons reagent In carbon disulfide for 4h; Inert atmosphere; Reflux;47%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

C28H58O2PSi(1+)*Cl(1-)

C28H58O2PSi(1+)*Cl(1-)

(all-E,2'S)-3',4'-didehydro-1',2'-dihydro-β,φ-carotin-1',2'-diol

(all-E,2'S)-3',4'-didehydro-1',2'-dihydro-β,φ-carotin-1',2'-diol

Conditions
ConditionsYield
Stage #1: trans-β-apo-8'-carotenal; C28H58O2PSi(1+)*Cl(1-) With sodium methylate In methanol; dichloromethane at 20℃; for 0.333333h; Wittig Olefination; Inert atmosphere;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;
43%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

diethyl 4-nitrobenzylphosphonate
2609-49-6

diethyl 4-nitrobenzylphosphonate

(7'E)-7'-(4-nitrophenyl)-7'-apo-β-carotene
148216-58-4

(7'E)-7'-(4-nitrophenyl)-7'-apo-β-carotene

Conditions
ConditionsYield
With sodium ethanolate37%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

<(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon
65243-75-6

<(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

(3'S,5'R)-Kryptocapsin

(3'S,5'R)-Kryptocapsin

Conditions
ConditionsYield
With sodium amide In toluene at 0℃; for 5h;37%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

C37H46

C37H46

Conditions
ConditionsYield
With sodium methylate In dimethyl sulfoxide at 65℃; for 3h;30%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

4-bromobenzyl triphenylphosphonium bromide
51044-13-4

4-bromobenzyl triphenylphosphonium bromide

C37H45Br

C37H45Br

Conditions
ConditionsYield
With sodium methylate In dimethyl sulfoxide at 65℃; for 3h;30%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

trans-3,7-Dimethyl-6,7-epoxy-2-octen-1-triphenylphosphoniumbromid

trans-3,7-Dimethyl-6,7-epoxy-2-octen-1-triphenylphosphoniumbromid

1',2'-Epoxy-1',2'-dihydro-β,ψ-carotin

1',2'-Epoxy-1',2'-dihydro-β,ψ-carotin

Conditions
ConditionsYield
With sodium ethanolate In ethanol; dichloromethane for 20h;25.5%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

(6S)-6,7-dihydroxy-O-isopropylidene-3-methyl-2,4-heptadienyl triphenylphosphonium bromide

(6S)-6,7-dihydroxy-O-isopropylidene-3-methyl-2,4-heptadienyl triphenylphosphonium bromide

(2'S)-16',17'-dinorplectaniaxanthin acetonide

(2'S)-16',17'-dinorplectaniaxanthin acetonide

Conditions
ConditionsYield
With sodium hydride In dichloromethane for 23h; Ambient temperature;16%
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

<(6S,4E)-6,7-dihydroxy-3,7-dimethyl-2,4-octadien-1-yl>triphenylphosphoniumbromid

<(6S,4E)-6,7-dihydroxy-3,7-dimethyl-2,4-octadien-1-yl>triphenylphosphoniumbromid

(all-E,2'S)-2'-acetoxy-3',4'-didehydro-1',2'-dihydro-β,φ-carotin-1'-ol

(all-E,2'S)-2'-acetoxy-3',4'-didehydro-1',2'-dihydro-β,φ-carotin-1'-ol

Conditions
ConditionsYield
In various solvent(s) for 72h; Heating;2%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

5',6'-dihydro-4'-apo-β,ψ-caroten-6'-one
105861-29-8

5',6'-dihydro-4'-apo-β,ψ-caroten-6'-one

Conditions
ConditionsYield
With potassium hydroxide
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

8'-Apo-β-carotene-8'-aldoxime

8'-Apo-β-carotene-8'-aldoxime

Conditions
ConditionsYield
With ethanol; hydroxylamine unter Stickstoff;
With pyridine; hydroxylamine hydrochloride at 60℃; for 4h;
trans-β-apo-8'-carotenal
1107-26-2

trans-β-apo-8'-carotenal

all-trans-8'-apo-β-carotenal-(8')-semicarbazone
119877-26-8

all-trans-8'-apo-β-carotenal-(8')-semicarbazone

1107-26-2Relevant articles and documents

Efficient oxidation of β?carotene in μ-carbido diiron octapropyltetraazaporphyrin–tBuOOH system

, ()

The oxidative decomposition of β?carotene mediated by μ-carbido diiron octapropyltetraazaporphyrin ([FeOPrTAP]2C)–tBuOOH system was investigated in benzene. Interaction between tBuOOH and the binuclear complex resulted in the generation of powerful high-oxidized species those are capable of oxidizing the employed substrate within the limits of several minutes. The explanation for such reactivity behavior involves the existence of a mixture of reactive intermediates in the reaction medium: more stable singly oxidized at the macrocyclic ligand π-cation radical as well as much more reactive dication species that is more contributing to the reaction rate. The introduction of imidazole into the coordination sphere of the initial diiron complex accelerates the β?carotene destruction because of generation of a powerful high-oxidizing species, which is capable of oxidizing β?carotene as well as the applied organic peroxide resulting in dioxygen release. Catalytic behavior of all the observed active intermediates was supported by recycling of the reaction under carotene adding. The quantitative characteristics of reactivity of studied systems were obtained and the possible reaction mechanisms were proposed.

Yokoyama,White

, p. 2481,2482 (1965)

Mild oxidative cleavage of β,β-carotene by dioxygen induced by a ruthenium porphyrin catalyst: Characterization of products and of some possible intermediates

Caris-Veyrat,Amiot,Ramasseul,Marchon

, p. 203 - 206 (2001)

Mild oxidative cleavage of β,β-carotene by dioxygen is induced by a ruthenium tetramesitylporphyrin catalyst, and it leads to the full possible range of β-apocarotenals and β-apocarotenones. The slow reaction kinetics allow the sequence of events leading to double bond cleavage over a period of 24 h to be monitored by HPLC-DAD and HPLC-MS.

Method for preparing beta-Apo-8'-carotenal

-

Paragraph 0030; 0031; 0035, (2016/11/21)

The invention discloses a method for preparing beta-Apo-8'-carotenal. The method includes steps of (1) synthesizing raw materials 2, 6, 6-trimethyl-1- cyclohexanemethanol and triphenylphosphine as raw materials into 2, 6, 6-trimethyl-1-cyclohexene methyl triphenylphosphine salt; (2) subjecting 2, 6, 6-trimethyl-1-cyclohexene methyl triphenylphosphine salt and 2, 6, 11, 15-tetramethyl-2, 4, 6, 8, 10, 12, 14-hexadecanoyl heptaene dialdehyde to wittig reaction to obtain beta-Apo-8'-carotenal. The method using 2, 6, 6-trimethyl-1- cyclohexanemethanol as raw materials is safe in reaction and is a novel method.

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