Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 15:12:44 UTC |
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Update Date | 2022-03-07 02:49:18 UTC |
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HMDB ID | HMDB0003240 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol |
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Description | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048 , 15003396 ). |
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Structure | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C 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 |
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Synonyms | Value | Source |
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(3R,3'r,15-cis)-b,b-Carotene-3,3'-diol | Generator | (3R,3'r,15-cis)-Β,β-carotene-3,3'-diol | Generator | (15Z)-Zeaxanthin | HMDB | (3R,3'r,15-cis)-Zeaxanthin | HMDB | (3R,3’R,15-cis)-zeaxanthin | HMDB | (3R,3’R,15-cis)-β,β-carotene-3,3’-diol | HMDB | 15-cis-Zeaxanthin | HMDB | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol | HMDB |
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Chemical Formula | C40H56O2 |
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Average Molecular Weight | 568.886 |
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Monoisotopic Molecular Weight | 568.428031043 |
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IUPAC Name | (1R)-4-[(1E,3E,5E,7E,9Z,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 |
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Traditional Name | 13Z-β,β-carotene-3R,3R'-diol |
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CAS Registry Number | 60046-54-0 |
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SMILES | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C |
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InChI Identifier | 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 |
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InChI Key | JKQXZKUSFCKOGQ-RFVVUROPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Tetraterpenoids |
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Direct Parent | Xanthophylls |
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Alternative Parents | |
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Substituents | - Xanthophyll
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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(3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C | 6200.6 | Standard polar | 33892256 | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C | 4801.7 | Standard non polar | 33892256 | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C | 4417.5 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol,1TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C\C=C(C)\C=C\C=C(C)\C=C\C2=C(C)C[C@@H](O[Si](C)(C)C)CC2(C)C)C(C)(C)C[C@H](O)C1 | 4759.2 | Semi standard non polar | 33892256 | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol,2TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C\C=C(C)\C=C\C=C(C)\C=C\C2=C(C)C[C@@H](O[Si](C)(C)C)CC2(C)C)C(C)(C)C[C@H](O[Si](C)(C)C)C1 | 4696.7 | Semi standard non polar | 33892256 | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol,1TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C\C=C(C)\C=C\C=C(C)\C=C\C2=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C)C(C)(C)C[C@H](O)C1 | 4957.1 | Semi standard non polar | 33892256 | (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol,2TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C\C=C(C)\C=C\C=C(C)\C=C\C2=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C)C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C1 | 5117.6 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol GC-MS ("(3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 10V, Negative-QTOF | splash10-014i-0001090000-762864ffd0f72009c688 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 20V, Negative-QTOF | splash10-014i-0104290000-79f130816293d1629a5c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 40V, Negative-QTOF | splash10-003b-0229210000-8aa487c6a883739666a2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 10V, Positive-QTOF | splash10-014i-0132890000-50be05fa861115532d66 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 20V, Positive-QTOF | splash10-0ue9-0215950000-140f155070c122eab02c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3R,3'R,15-cis)-beta,beta-Carotene-3,3'-diol 40V, Positive-QTOF | splash10-0v00-0039600000-2725b4335e7d4d6e49c2 | 2021-09-24 | Wishart Lab | View Spectrum |
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