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β-Apo-8'-carotenal

Alias: β​Apo​8'​carotenal; β ​Apo ​8' ​carotenal
β-Apo-8'-carotenal (Apocarotenal) is a provitamin A carotenoid and an inducer of CYP1A1 and CYP1A2 in rats.
β-Apo-8'-carotenal
β-Apo-8'-carotenal Chemical Structure CAS No.: 1107-26-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
β-Apo-8'-carotenal (Apocarotenal) is a provitamin A carotenoid and an inducer of CYP1A1 and CYP1A2 in rats. β-Apo-8'-carotenal is found in many fruits and vegetables.
β-Apo-8'-carotenal (CAS#: 1107-26-2) is a carotenoid derivative and a natural pigment found in fruits and vegetables. It is a metabolite of β-carotene and is used as a food coloring agent and a provitamin A source. It has been studied for its antioxidant properties and potential protective effects against oxidative stress. It is not a drug but is used in dietary supplements.
Biological Activity I Assay Protocols (From Reference)
Targets
β-Apo-8'-carotenal does not have a specific pharmacological target. Its biological activity is primarily through its antioxidant and retinoid activity. It can be converted to retinoic acid and may act as a weak agonist of retinoic acid receptors (RARs), modulating gene expression. It also scavenges free radicals and protects cells from lipid peroxidation.
ln Vitro
In vitro, β-Apo-8'-carotenal exhibits antioxidant activity by quenching singlet oxygen and peroxyl radicals. It inhibits lipid peroxidation in rat liver microsomes with an IC50 of 5 µM. It shows moderate protection against oxidative damage in cultured human fibroblasts at concentrations of 1-10 µM. It has no significant cytotoxicity up to 50 µM.
ln Vivo
In vivo, β-Apo-8'-carotenal has been shown to increase plasma vitamin A levels in vitamin A-deficient animals. In rats, oral administration (10-50 mg/kg) for 7 days restored retinol levels and improved night vision. It also reduced oxidative stress markers in a rat model of diabetes (20 mg/kg, p.o.) and protected against carbon tetrachloride-induced hepatotoxicity.
Enzyme Assay
The in vitro antioxidant assay is performed using the DPPH radical scavenging method. β-Apo-8'-carotenal is dissolved in ethanol and incubated with DPPH (0.1 mM) for 30 min at 25°C. The decrease in absorbance at 517 nm is measured. Trolox is used as a standard. The compound's IC50 is determined. For lipid peroxidation, rat liver microsomes are incubated with Fe²⁺/ascorbate and varying concentrations of the compound; malondialdehyde is measured by TBARS assay.
Cell Assay
For in vitro cell-based assays, human dermal fibroblasts are seeded in 96-well plates and treated with β-Apo-8'-carotenal (1-50 µM) for 24 h, followed by oxidative stress induced by H₂O₂ (200 µM) for 4 h. Cell viability is measured by MTT. Intracellular ROS is detected by DCFH-DA fluorescence. Gene expression of antioxidant enzymes (SOD, CAT) is assessed by RT-qPCR.
Animal Protocol
In vivo studies are typically performed in male Wistar rats (200-250 g). β-Apo-8'-carotenal is dissolved in corn oil and administered orally at doses of 10, 20, and 50 mg/kg daily for 7-14 days. For vitamin A deficiency models, rats are fed a vitamin A-free diet for 4 weeks before treatment. Blood and liver samples are collected for retinol and retinoic acid analysis by HPLC. Oxidative stress markers are measured in liver homogenates.
ADME/Pharmacokinetics
Pharmacokinetic data for β-Apo-8'-carotenal are limited. In humans, it is absorbed from the intestine and converted to retinoic acid. The plasma half-life is approximately 2-3 h. It is metabolized in the liver and excreted in bile and urine. Bioavailability is moderate and depends on fat co-administration. Plasma protein binding is about 80%.
Toxicity/Toxicokinetics
β-Apo-8'-carotenal has low toxicity. The oral LD50 in rats is >5000 mg/kg. It is not mutagenic in the Ames test. In subchronic studies, doses up to 100 mg/kg/day for 90 days showed no adverse effects. It is considered safe as a food additive (E160e) and is generally recognized as safe (GRAS) at approved levels.
References

[1]. 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.

Additional Infomation
8'-apo-β,psi-carotene-8'-aldehyde is an apocarotenoid triterpenoid compound derived from the oxidative degradation of the β,β-carotene skeleton at the 8' position. It is an enaldehyde and also an apocarotenoid triterpenoid compound. Apocarotenoid aldehydes have been reported to be found in citrus fruits (Citrus reticulata), peppers (Capsicum annuum), and other organisms with relevant data.
β-Apo-8'-carotenal is approved as a food coloring agent in many countries. It is also used in dietary supplements as a provitamin A. It has been investigated for its potential to prevent vitamin A deficiency and as an antioxidant. However, it is not a therapeutic drug. Clinical studies are limited to nutritional applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₃₀H₄₀O
Molecular Weight
416.64
Exact Mass
416.307
CAS #
1107-26-2
PubChem CID
5478003
Appearance
Blue to dark blue solid powder
Density
0.9±0.1 g/cm3
Boiling Point
575.7±19.0 °C at 760 mmHg
Melting Point
138-141ºC
Flash Point
273.8±13.8 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.553
LogP
9.82
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
9
Heavy Atom Count
31
Complexity
887
Defined Atom Stereocenter Count
0
SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=O)/C)/C
InChi Key
DFMMVLFMMAQXHZ-DOKBYWHISA-N
InChi Code
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+
Chemical Name
(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
Synonyms
β​Apo​8'​carotenal; β ​Apo ​8' ​carotenal
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~1 mg/mL (~2.40 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 4.17 mg/mL (10.01 mM) in Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4002 mL 12.0008 mL 24.0015 mL
5 mM 0.4800 mL 2.4002 mL 4.8003 mL
10 mM 0.2400 mL 1.2001 mL 2.4002 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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