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10810

Sigma-Aldrich

trans-β-Apo-8′-carotenal

≥96.0% (UV)

Synonym(s):

Apocarotenal

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About This Item

Empirical Formula (Hill Notation):
C30H40O
CAS Number:
1107-26-2
Molecular Weight:
416.64
Beilstein:
2064131
EC Number:
214-171-6
MDL number:
MFCD00042626
UNSPSC Code:
12352205
PubChem Substance ID:
57646819
NACRES:
NA.79

biological source

synthetic

Assay

≥96.0% (UV)

form

powder

loss

≤0.5% loss on drying, 20 °C (HV)

mp

137-141 °C

solubility

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

storage temp.

−20°C

SMILES string

[H]C(=O)\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+

InChI key

DFMMVLFMMAQXHZ-DOKBYWHISA-N

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Application


  • Tackling the challenge of selective analytical clean-up of complex natural extracts: the curious case of chlorophyll removal: This study outlines a methodology for the selective analytical clean-up of complex natural extracts, which can be applied to enhance the purity and stability of trans-β-Apo-8′-carotenal, particularly useful in the context of life science manufacturing and research and development. This approach is crucial for maintaining the integrity of bioactive compounds during synthesis and storage (Bijttebier et al., 2014).

Biochem/physiol Actions

Natural carotenoid that is formed from β-carotene in vivo and is an inducer of cytochrome P450 1A (CYP1A) in rats and in Ah-receptor-responsive mice.

Other Notes

Internal standard in the detection of citrus carotenoids by reversed-phase HPLC.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yuka Matsushita-Ishiodori et al.
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Feng Liu et al.
Proteomics, 6(9), 2673-2692 (2006-04-06)
Hematopoietic stem cells are capable of self-renewal and differentiation into different hematopoietic lineages. To gain a comprehensive understanding of hematopoietic stem/progenitor cells, a systematic proteomic survey of human CD34+ cells collected from human umbilical cord blood was performed, in which
C Duszka et al.
The Journal of nutrition, 126(10), 2550-2556 (1996-10-01)
The purposes of this study were to determine the location of beta-carotene dioxygenase (EC 1.13.11.21) activity within the rat gastrointestinal tract, within the villus and within enterocytes, and to identify the metabolites produced in each intestinal fraction. In Wistar female
J R Kanofsky et al.
Photochemistry and photobiology, 73(4), 349-358 (2001-05-03)
A cationic carotenoid derivative (GRP-carotenal) was synthesized by the reaction of Girard's reagent P and beta-apo-8'-carotenal. The singlet-oxygen quenching constants for GRP-carotenal were 1.3 +/- 0.1 x 10(10) and 1.0 +/- 0.1 x 10(10) M-1 s-1 in acetonitrile and in
G Drikos et al.
European biophysics journal : EBJ, 16(4), 193-205 (1988-01-01)
During the visual process, light absorption in the 11-cis retinylidene chromophore leads to a rapid cis-trans-isomerization which initiates the phototransduction step. Important spectroscopic properties of this chromophore can be derived from polarized UV-absorption spectra of crystalline 11-cis-retinal if a parallel
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