8,8'-DIAPOCAROTENEDIOIC ACID

Iupac Name：(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,
14-heptaenedioic acid

Molecular Weight：328.40216

Modify Date.: 2023-02-09 23:31

Introduction: Experimental treatment of arteriosclerosis byincreasing oxygen diffusion through arterial walls,thus decreasing buildup of cholesterol. View more+

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1. Names and Identifiers

1.1 Name: 8,8'-DIAPOCAROTENEDIOIC ACID
1.2 Synonyms: (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-Tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioic acid (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid (2E,4E,8E,12E,14E)-2,6,11,15-Tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioic acid 2,4,6,8,10,12,14-Hexadecaheptaenedioic acid, 2,6,11,15-tetramethyl-, (2E,4E,6E,8E,10E,12E,14E)- 2,4,6,8,10,12,14-Hexadecaheptaenedioic acid, 2,6,11,15-tetramethyl-, (2E,4E,8E,12E,14E)- 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid 2,6,11,15-TETRAMETHYLHEXADECA-2,4,6,8,10,12,14-HEPTAENEDOIC ACID 8,8'-Diapo-8,8'-carotenedioic acid 8,8'-Diapocarotene-8,8'-dioic acid 8,8'-diapo-psi,psi-carotenedioic acid 8,8'-Diapo-y,y-carotenedioic Acid all-trans-8,8'-diapocarotene-8,8'-dioic acid Alpha-Crocetin carotenoid dicarboxylic acid CROCETIN CROCETIN, TRANS- EINECS 248-708-0 FEMA 2998 Natural yellow 6 roceic acid transcrocetin TRANS-CROCETIN

1.3 CAS No.: 27876-94-4

1.4 CID: 5281232

1.5 EINECS(EC#): 248-708-0

1.6 Molecular Formula: C20H24O4 (isomer)

1.7 Inchi: InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+

1.8 InChkey: PANKHBYNKQNAHN-MQQNZMFNSA-N

1.9 Canonical Smiles: CC(=CC=CC=C(C)C=CC=C(C)C(=O)O)C=CC=C(C)C(=O)O

1.10 Isomers Smiles: C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)O)/C)/C)/C=C/C=C(/C(=O)O)\C

2. Properties

2.1 Density: 1.085

2.1 Melting point: 285 oC

2.1 Boiling point: 585.1°Cat760mmHg

2.1 Refractive index: 1.558

2.1 Flash Point: 321.7°C

2.1 Precise Quality: 328.16700

2.1 PSA: 74.60000

2.1 logP: 4.60940

2.1 Appearance: Red solid

2.2 Chemical Properties: Red, rhomboid crystals.Soluble in pyridine and dilute sodium hydroxide;slightly soluble in water and organic solvents. Combustible.

2.3 Color/Form: Red cryst.

2.4 pKa: 4.39±0.19(Predicted)

2.5 StorageTemp: Inert atmosphere,Store in freezer, under -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement.

3.2 Usage: Experimental treatment of arteriosclerosis byincreasing oxygen diffusion through arterial walls,thus decreasing buildup of cholesterol.

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Synthesis Route

27876-94-4Total: 2 Synthesis Route

42553-65-1 105 Suppliers

27876-94-4 47 Suppliers

Literatures:
RIKEN VITAMIN CO., LTD. Patent: WO2004/78695 A1, 2004 ; Location in patent: Page 16 ;
Yield: null

35482-80-5

27876-94-4 47 Suppliers

Literatures:
Schwieter,U. et al. Helvetica Chimica Acta, 1971 , vol. 54, p. 2447 - 2459
Yield: null

7. Precursor and Product

precursor:

42553-65-1

35482-80-5

8. Other Information

8.0 Chemical Properties: Red, rhomboid crystals.Soluble in pyridine and dilute sodium hydroxide; slightly soluble in water and organic solvents. Combustible.

8.1 Uses: Experimental treatment of arteriosclerosis by increasing oxygen diffusion through arterial walls, thus decreasing buildup of cholesterol.

8.2 Definition: ChEBI: A 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement.

8.3 体外研究: Transcrocetin (trans-Crocetin), a saffron metabolite originating from the crocin apocarotenoids, has been shown to exert strong NMDA receptor affinity and is thought to be responsible for the CNS activity of saffron.To ensure unchanged viability of Caco-2 cells throughout the transport experiments, cellular mitochondrial dehydrogenase activity of Caco-2 cells is measured by MTT assay after a 24 h incubation period with the test compounds: Hydroalcoholic saffron extract saffron extract (SE, 0.5-1 mg/mL) and crocin-1 (250-1000 μM) reveal no negative significant changes in cellular viability. Transcrocetin at 10 μM level does not change viability while higher concentrations (40-160 μM) reduces significantly cellular viability.

8.4 Uses: Crocetin is a carotenoid derived from saffron, and is shown to have anticancer effects in both human adenocarcinoma gastric cancer cells and rat model of gastric cancer.

9. Computational chemical data

Molecular Weight: 328.40216g/mol
Molecular Formula: C₂₀H₂₄O₄
Compound Is Canonicalized: True
XLogP3-AA: 5.4
Exact Mass: 328.16745924
Monoisotopic Mass: 328.16745924
Complexity: 608
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 74.6
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 7
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAADACAgAACCAAAAgCIAiDSCAAAAAAgAAAICAEAAEgIBAAAAQAAUAAAAAAIkYIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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