(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

• ChemBase ID: 130236
• Molecular Formular: C40H56O2
• Molecular Mass: 568.87144
• Monoisotopic Mass: 568.42803103
• SMILES: CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C[C@H](CC1(C)C)O)C)\C)\C)/C)/C
• Canonical SMILES: O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C)\C)/C)/C)C
• InChI: InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
• InChIKey: JKQXZKUSFCKOGQ-QAYBQHTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol; (1R)-4-{18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol
• IUPAC Traditional name: zeaxanthin; (1R)-4-{18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol
• Synonyms: β,β-carotene-3,3'-diol; Zeaxanthin; β,β-Carotene-3,3′-diol; Zeaxanthin; β,β-胡萝卜素-3,3′-二醇; 玉米黄质

Database IDs

• CAS Number: 144-68-3
• EC Number: 205-636-4
• MDL Number: MFCD08435940
• PubChem SID: 24848797; 162224516
• PubChem CID: 5280899
• CHEBI ID: 27547
• Chemspider ID: 4444421
• Unique Ingredient Identifier: CV0IB81ORO
• Wikipedia Title: Zeaxanthin

CALCULATED PROPERTIES

• Acid pKa: 18.907213
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 8.350644
• LogD (pH = 7.4): 8.350644
• Log P: 8.350644
• Molar Refractivity: 194.9508 cm^3
• Polarizability: 71.71594 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: insol. in water
• Apperance: orange-red
• Melting Point: 215.5°C

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (TLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C40H56O2

DETAILS

Sigma Aldrich - 14681

Biochem/physiol Actions
Carotenoid pigment that contributes to the color of paprika. Zeaxanthin accumulates within the eye retina and is thought to decrease the incidence of macular degeneration.