| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-11 17:34:08 UTC |
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| Update Date | 2022-03-07 02:52:23 UTC |
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| HMDB ID | HMDB0030008 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | delta-Tocotrienol |
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| Description | delta-Tocotrienol, also known as 8-methyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, delta-tocotrienol is considered to be a quinone lipid molecule. delta-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. delta-Tocotrienol is found in American cranberry and palm oil. It is a nutriceutical with anticancer properties and a positive influence on the blood lipid profile. |
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| Structure | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1 InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1 |
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| Synonyms | | Value | Source |
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| (2R)-2,8-Dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol | ChEBI | | Δ-tocotrienol | Generator | | Tocotrienol, delta | HMDB | | (2R)-3,4-Dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-ol | HMDB | | (R)-delta-Tocotrienol | HMDB | | (R)-Δ-tocotrienol | HMDB | | 8-Methyltocotrienol | HMDB | | D-delta-Tocotrienol | HMDB | | D-Δ-tocotrienol | HMDB | | delta-Tocotrienol | HMDB |
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| Chemical Formula | C27H40O2 |
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| Average Molecular Weight | 396.615 |
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| Monoisotopic Molecular Weight | 396.302830528 |
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| IUPAC Name | (2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol |
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| Traditional Name | delta tocotrienol |
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| CAS Registry Number | 25612-59-3 |
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| SMILES | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1 |
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| InChI Identifier | InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1 |
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| InChI Key | ODADKLYLWWCHNB-LDYBVBFYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain. |
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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 | Quinone and hydroquinone lipids |
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| Direct Parent | Tocotrienols |
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| Alternative Parents | |
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| Substituents | - Tocotrienol
- Diterpenoid
- 1-benzopyran
- Benzopyran
- Chromane
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Not Available | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | |
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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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022. | 10.5 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 26.0195 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.31 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 3656.7 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 705.4 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 314.2 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 346.1 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 287.7 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1196.7 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 1080.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 90.7 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 2312.6 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 839.0 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 1749.2 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 868.1 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 533.0 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 323.5 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 631.3 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 8.8 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - delta-Tocotrienol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 10V, Positive-QTOF | splash10-000b-0729000000-bdb3f601da6568da91fe | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 20V, Positive-QTOF | splash10-000i-1910000000-abbd9af3e2be0c682cfe | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 40V, Positive-QTOF | splash10-000i-3920000000-7d0b193d8a3c3a3a5967 | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 10V, Negative-QTOF | splash10-0002-0109000000-5ada9ae99b1c0f7f1258 | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 20V, Negative-QTOF | splash10-000b-0709000000-22c37c4db5a8d82525ff | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 40V, Negative-QTOF | splash10-002r-0913000000-c3d3a5ed1080b2af167f | 2019-02-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 10V, Negative-QTOF | splash10-0002-0009000000-6a4833272e2724162c45 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 20V, Negative-QTOF | splash10-000j-0916000000-9b31c3c1cdaceab36ab0 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 40V, Negative-QTOF | splash10-01t9-1913000000-c21cc59c09a4319fdf57 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 10V, Positive-QTOF | splash10-0002-4297000000-0ab38ee133d435f0f5d5 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 20V, Positive-QTOF | splash10-00li-5490000000-6c3f81f0aef0bd5e6754 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Tocotrienol 40V, Positive-QTOF | splash10-005c-8900000000-1b24b2b5c3b9fee9a43a | 2021-09-24 | Wishart Lab | View Spectrum |
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