| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-12 00:16:10 UTC |
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| Update Date | 2022-03-07 02:55:59 UTC |
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| HMDB ID | HMDB0038921 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 5'-Methoxycurcumin |
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| Description | 5'-Methoxycurcumin belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. 5'-Methoxycurcumin has been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and root vegetables. This could make 5'-methoxycurcumin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5'-Methoxycurcumin. |
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| Structure | COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC(OC)=C1O InChI=1S/C22H22O7/c1-27-19-10-14(6-9-18(19)25)4-7-16(23)13-17(24)8-5-15-11-20(28-2)22(26)21(12-15)29-3/h4-12,25-26H,13H2,1-3H3/b7-4+,8-5+ |
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| Synonyms | Not Available |
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| Chemical Formula | C22H22O7 |
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| Average Molecular Weight | 398.4059 |
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| Monoisotopic Molecular Weight | 398.136553058 |
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| IUPAC Name | (1E,6E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione |
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| Traditional Name | (1E,6E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC(OC)=C1O |
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| InChI Identifier | InChI=1S/C22H22O7/c1-27-19-10-14(6-9-18(19)25)4-7-16(23)13-17(24)8-5-15-11-20(28-2)22(26)21(12-15)29-3/h4-12,25-26H,13H2,1-3H3/b7-4+,8-5+ |
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| InChI Key | MQJGAHXKAZGEGI-NSLJXJERSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Diarylheptanoids |
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| Sub Class | Linear diarylheptanoids |
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| Direct Parent | Curcuminoids |
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| Alternative Parents | |
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| Substituents | - Curcumin
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- M-dimethoxybenzene
- Dimethoxybenzene
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Styrene
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1,3-diketone
- Phenol
- Monocyclic benzene moiety
- 1,3-dicarbonyl compound
- Benzenoid
- Acryloyl-group
- Enone
- Alpha,beta-unsaturated ketone
- Ketone
- Ether
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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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 | |
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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 | 145 - 146 °C | 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 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. Predicted by Afia on May 17, 2022. | 7.78 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 11.5184 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.0 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 26.5 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 2364.7 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 198.1 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 176.2 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 162.2 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 104.6 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 576.0 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 | 395.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 139.7 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1210.1 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 439.2 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 | 1128.8 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 324.3 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 404.3 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 272.1 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 246.7 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 | 8.1 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| 5'-Methoxycurcumin,1TMS,isomer #1 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C | 3754.6 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TMS,isomer #2 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O | 3713.1 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TMS,isomer #3 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O | 3961.9 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TMS,isomer #4 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O | 3932.7 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TMS,isomer #1 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C | 3711.6 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TMS,isomer #2 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3911.9 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TMS,isomer #3 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3931.0 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TMS,isomer #4 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O | 3850.6 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TMS,isomer #5 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O | 3864.7 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TMS,isomer #1 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3853.2 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TMS,isomer #1 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3754.0 | Standard non polar | 33892256 | | 5'-Methoxycurcumin,3TMS,isomer #2 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3862.7 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TMS,isomer #2 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C | 3756.3 | Standard non polar | 33892256 | | 5'-Methoxycurcumin,1TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4054.5 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O | 3999.4 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TBDMS,isomer #3 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O | 4252.8 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,1TBDMS,isomer #4 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O | 4226.2 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TBDMS,isomer #1 | COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4267.1 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TBDMS,isomer #2 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4481.2 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TBDMS,isomer #3 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4501.9 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TBDMS,isomer #4 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O | 4440.3 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,2TBDMS,isomer #5 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O | 4457.0 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TBDMS,isomer #1 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4635.5 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TBDMS,isomer #1 | COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4352.6 | Standard non polar | 33892256 | | 5'-Methoxycurcumin,3TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4650.8 | Semi standard non polar | 33892256 | | 5'-Methoxycurcumin,3TBDMS,isomer #2 | COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C | 4354.3 | Standard non polar | 33892256 |
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