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β-​Apo-​8'-​carotenal

Names

[ CAS No. ]:
1107-26-2

[ Name ]:
β-​Apo-​8'-​carotenal

[Synonym ]:
8'-Apo-β-carotenal
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-Tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10,12,14,16-heptadecaoctaenal
Apocarotenal
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-Tetramethyl-17-(2,6,6-trimethylcyclohex-1-en-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
all-trans-8'-apo-β-carotenal
C.I. Food Orange 6
(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
EINECS 214-171-6
8'-apo-beta,psi-caroten-8'-al
β-Apocarotenal
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)-
trans-β-Apo-8′-carotenal
all-trans-β-Apo-8'-carotenal
trans-β-Apo-8'-carotenal
Colour Index, Food Orange 6
MFCD00042626
β-apo-Carotenal

Biological Activity

[Description]:

β-Apo-8'-carotenal (Apocarotenal), a provitamin A carotenoid, is an inducer of CYPlA1 and CYPlA2 in rat. β-Apo-8'-carotenal is present in many fruits and vegetables[1].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

[Target]

CYP1A1

CYP1A2


[References]

[1]. Gradelet S, et al.beta-Apo-8'-carotenal, but not beta-carotene, is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat.Xenobiotica. 1996 Sep;26(9):909-19.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
575.7±19.0 °C at 760 mmHg

[ Melting Point ]:
138-141ºC

[ Molecular Formula ]:
C30H40O

[ Molecular Weight ]:
416.638

[ Flash Point ]:
273.8±13.8 °C

[ Exact Mass ]:
416.307922

[ PSA ]:
17.07000

[ LogP ]:
9.82

[ Appearance of Characters ]:
suspension (oily)

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.553

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
chloroform: 1 mg/mL, clear to very faintly turbid, intense red-orange

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CD9115000
CHEMICAL NAME :
8'-Apo-beta,psi-carotenal
CAS REGISTRY NUMBER :
1107-26-2
BEILSTEIN REFERENCE NO. :
2064131
LAST UPDATED :
199701
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C30-H40-O

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FAONAU FAO Nutrition Meetings Report Series. (Rome, Italy) No.?-57, 1948-77. Discontinued. Volume(issue)/page/year: 38B,34,1966 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
85 gm/kg/34W-I
TOXIC EFFECTS :
Related to Chronic Data - changes in testicular weight
REFERENCE :
FAONAU FAO Nutrition Meetings Report Series. (Rome, Italy) No.?-57, 1948-77. Discontinued. Volume(issue)/page/year: 38B,34,1966

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
CD9115000

Synthetic Route

Precursor & DownStream

Articles

The formation, occurrence, and function of β-apocarotenoids: β-carotene metabolites that may modulate nuclear receptor signaling.

Am. J. Clin. Nutr. 96(5) , 1189S-92S, (2012)

β-Carotene is the major dietary source of provitamin A. Central cleavage of β-carotene yields 2 molecules of retinal followed by further oxidation to retinoic acid. Eccentric cleavage of β-carotene oc...

Structural basis of carotenoid cleavage: from bacteria to mammals.

Arch. Biochem. Biophys. 539(2) , 203-13, (2013)

Carotenoids and their metabolic derivatives serve critical functions in both prokaryotic and eukaryotic cells, including pigmentation, photoprotection and photosynthesis as well as cell signaling. The...

beta-Apo-8'-carotenal, but not beta-carotene, is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat.

Xenobiotica 26(9) , 909-19, (1996)

1. The catalytic activities of several phase I and II xenobiotic-metabolizing enzymes and their immunochemical detection have been investigated in liver microsomes and cytosol of the male rat, which h...


More Articles


Related Compounds