Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 04:32:46 UTC |
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Updated at | 2022-09-10 04:32:47 UTC |
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NP-MRD ID | NP0295526 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | β-d-glucosyl crocetin |
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Description | Beta-D-glucosyl crocetin, also known as crocetin b-D-glucosyl ester, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. β-d-glucosyl crocetin is found in Crocus sativus and Gardenia jasminoides. It was first documented in 2009 (PMID: 19325516). Based on a literature review a significant number of articles have been published on beta-D-glucosyl crocetin (PMID: 35669709) (PMID: 32127777) (PMID: 29502833) (PMID: 25075549). |
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Structure | C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C26H34O9/c1-16(11-7-13-18(3)24(31)32)9-5-6-10-17(2)12-8-14-19(4)25(33)35-26-23(30)22(29)21(28)20(15-27)34-26/h5-14,20-23,26-30H,15H2,1-4H3,(H,31,32)/b6-5+,11-7+,12-8+,16-9+,17-10+,18-13+,19-14+/t20-,21-,22+,23-,26+/m1/s1 |
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Synonyms | Value | Source |
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all-trans-Crocetin mono(beta-D-glucosyl) ester | ChEBI | Crocetin beta-D-glucopyranosyl ester | ChEBI | Crocetin beta-D-glucosyl ester | ChEBI | Crocetin mono(beta-D-glucosyl) ester | ChEBI | trans-Crocetin beta-D-glucosyl ester | ChEBI | all-trans-Crocetin mono(b-D-glucosyl) ester | Generator | all-trans-Crocetin mono(β-D-glucosyl) ester | Generator | Crocetin b-D-glucopyranosyl ester | Generator | Crocetin β-D-glucopyranosyl ester | Generator | Crocetin b-D-glucosyl ester | Generator | Crocetin β-D-glucosyl ester | Generator | Crocetin mono(b-D-glucosyl) ester | Generator | Crocetin mono(β-D-glucosyl) ester | Generator | trans-Crocetin b-D-glucosyl ester | Generator | trans-Crocetin β-D-glucosyl ester | Generator | b-D-Glucosyl crocetin | Generator | Β-D-glucosyl crocetin | Generator |
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Chemical Formula | C26H34O9 |
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Average Mass | 490.5490 Da |
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Monoisotopic Mass | 490.22028 Da |
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IUPAC Name | (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoic acid |
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Traditional Name | β-D-glucosyl crocetin |
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CAS Registry Number | Not Available |
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SMILES | C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C26H34O9/c1-16(11-7-13-18(3)24(31)32)9-5-6-10-17(2)12-8-14-19(4)25(33)35-26-23(30)22(29)21(28)20(15-27)34-26/h5-14,20-23,26-30H,15H2,1-4H3,(H,31,32)/b6-5+,11-7+,12-8+,16-9+,17-10+,18-13+,19-14+/t20-,21-,22+,23-,26+/m1/s1 |
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InChI Key | ZVGODNZUEWDIPM-YXRLTKITSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
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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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Saccharolipid
- Long-chain fatty acid
- Hexose monosaccharide
- Branched fatty acid
- Fatty acid ester
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Sugar acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Unsaturated fatty acid
- Monosaccharide
- Oxane
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Secondary alcohol
- Carboxylic acid ester
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Polyol
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Ahrazem O, Diretto G, Rambla JL, Rubio-Moraga A, Lobato-Gomez M, Frusciante S, Argandona J, Presa S, Granell A, Gomez-Gomez L: Engineering high levels of saffron apocarotenoids in tomato. Hortic Res. 2022 Mar 23;9:uhac074. doi: 10.1093/hr/uhac074. eCollection 2022. [PubMed:35669709 ]
- Mir MA, Ganai SA, Mansoor S, Jan S, Mani P, Masoodi KZ, Amin H, Rehman MU, Ahmad P: Isolation, purification and characterization of naturally derived Crocetin beta-d-glucosyl ester from Crocus sativus L. against breast cancer and its binding chemistry with ER-alpha/HDAC2. Saudi J Biol Sci. 2020 Mar;27(3):975-984. doi: 10.1016/j.sjbs.2020.01.018. Epub 2020 Jan 27. [PubMed:32127777 ]
- Liu J, Chen N, Yang J, Yang B, Ouyang Z, Wu C, Yuan Y, Wang W, Chen M: An integrated approach combining HPLC, GC/MS, NIRS, and chemometrics for the geographical discrimination and commercial categorization of saffron. Food Chem. 2018 Jul 1;253:284-292. doi: 10.1016/j.foodchem.2018.01.140. Epub 2018 Feb 2. [PubMed:29502833 ]
- Valle Garcia-Rodriguez M, Serrano-Diaz J, Tarantilis PA, Lopez-Corcoles H, Carmona M, Alonso GL: Determination of saffron quality by high-performance liquid chromatography. J Agric Food Chem. 2014 Aug 13;62(32):8068-74. doi: 10.1021/jf5019356. Epub 2014 Aug 5. [PubMed:25075549 ]
- Maggi L, Carmona M, Zalacain A, Tome MM, Murcia MA, Alonso GL: Parabens as agents for improving crocetin esters' shelf-life in aqueous saffron extracts. Molecules. 2009 Mar 16;14(3):1160-70. doi: 10.3390/molecules14031160. [PubMed:19325516 ]
- LOTUS database [Link]
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