Record Information |
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Version | 1.0 |
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Created at | 2022-04-27 21:57:24 UTC |
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Updated at | 2022-04-27 21:57:24 UTC |
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NP-MRD ID | NP0050566 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Cryptoxanthin glucoside |
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Description | Cryptoxanthin glucoside 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. Thus, cryptoxanthin glucoside is considered to be an isoprenoid. Cryptoxanthin glucoside is found in Erwinia herbicola, Erwinia uredovora and Thermus thermophilus. It was first documented in 2016 (PMID: 27385558). Based on a literature review a significant number of articles have been published on Cryptoxanthin glucoside (PMID: 30705834) (PMID: 31718836) (PMID: 30724264) (PMID: 27812831). |
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Structure | C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(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@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C46H66O6/c1-31(18-13-20-33(3)23-25-38-35(5)22-15-27-45(38,7)8)16-11-12-17-32(2)19-14-21-34(4)24-26-39-36(6)28-37(29-46(39,9)10)51-44-43(50)42(49)41(48)40(30-47)52-44/h11-14,16-21,23-26,37,40-44,47-50H,15,22,27-30H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,31-16+,32-17+,33-20+,34-21+/t37-,40-,41-,42+,43-,44-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C46H66O6 |
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Average Mass | 715.0280 Da |
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Monoisotopic Mass | 714.48594 Da |
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IUPAC Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-yl]oxy}oxane-3,4,5-triol |
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Traditional Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-yl]oxy}oxane-3,4,5-triol |
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CAS Registry Number | Not Available |
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SMILES | C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(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@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C46H66O6/c1-31(18-13-20-33(3)23-25-38-35(5)22-15-27-45(38,7)8)16-11-12-17-32(2)19-14-21-34(4)24-26-39-36(6)28-37(29-46(39,9)10)51-44-43(50)42(49)41(48)40(30-47)52-44/h11-14,16-21,23-26,37,40-44,47-50H,15,22,27-30H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,31-16+,32-17+,33-20+,34-21+/t37-,40-,41-,42+,43-,44-/m1/s1 |
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InChI Key | ZHJIWERYMKQKHH-XFNMZINASA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | 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 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
- Terpene glycoside
- O-glycosyl compound
- Glycosyl compound
- Oxane
- Monosaccharide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 | - Escudero-Lopez B, Cerrillo I, Gil-Izquierdo A, Hornero-Mendez D, Herrero-Martin G, Berna G, Medina S, Ferreres F, Martin F, Fernandez-Pachon MS: Effect of thermal processing on the profile of bioactive compounds and antioxidant capacity of fermented orange juice. Int J Food Sci Nutr. 2016 Nov;67(7):779-88. doi: 10.1080/09637486.2016.1204428. Epub 2016 Jul 7. [PubMed:27385558 ]
- Vila E, Hornero-Mendez D, Azziz G, Lareo C, Saravia V: Carotenoids from heterotrophic bacteria isolated from Fildes Peninsula, King George Island, Antarctica. Biotechnol Rep (Amst). 2019 Jan 11;21:e00306. doi: 10.1016/j.btre.2019.e00306. eCollection 2019 Mar. [PubMed:30705834 ]
- Tkacz K, Wojdylo A, Turkiewicz IP, Ferreres F, Moreno DA, Nowicka P: UPLC-PDA-Q/TOF-MS profiling of phenolic and carotenoid compounds and their influence on anticholinergic potential for AChE and BuChE inhibition and on-line antioxidant activity of selected Hippophae rhamnoides L. cultivars. Food Chem. 2020 Mar 30;309:125766. doi: 10.1016/j.foodchem.2019.125766. Epub 2019 Oct 31. [PubMed:31718836 ]
- Lekala CS, Madani KSH, Phan ADT, Maboko MM, Fotouo H, Soundy P, Sultanbawa Y, Sivakumar D: Cultivar-specific responses in red sweet peppers grown under shade nets and controlled-temperature plastic tunnel environment on antioxidant constituents at harvest. Food Chem. 2019 Mar 1;275:85-94. doi: 10.1016/j.foodchem.2018.09.097. Epub 2018 Sep 17. [PubMed:30724264 ]
- Dabbou S, Maatallah S, Castagna A, Guizani M, Sghaeir W, Hajlaoui H, Ranieri A: Carotenoids, Phenolic Profile, Mineral Content and Antioxidant Properties in Flesh and Peel of Prunus persica Fruits during Two Maturation Stages. Plant Foods Hum Nutr. 2017 Mar;72(1):103-110. doi: 10.1007/s11130-016-0585-y. [PubMed:27812831 ]
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