| Record Information |
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| Version | 2.0 |
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| Created at | 2009-04-06 16:22:43 UTC |
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| Updated at | 2024-09-03 04:18:55 UTC |
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| NP-MRD ID | NP0001344 |
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| Natural Product DOI | https://doi.org/10.57994/1564 |
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| Secondary Accession Numbers | |
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| Natural Product Identification |
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| Common Name | Vanillin |
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| Description | Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. |
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| Structure | InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 |
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| Synonyms | | Value | Source |
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| 3-Methoxy-4-hydroxybenzaldehyde | ChEBI | | 4-Formyl-2-methoxyphenol | ChEBI | | 4-Hydroxy-3-methoxy-benzaldehyde | ChEBI | | 4-Hydroxy-3-methoxybenzaldehyde | ChEBI | | 4-Hydroxy-m-anisaldehyde | ChEBI | | Methylprotocatechuic aldehyde | ChEBI | | p-Hydroxy-m-methoxybenzaldehyde | ChEBI | | p-Vanillin | ChEBI | | Vaniline | ChEBI | | Vanillaldehyde | ChEBI | | Vanillic aldehyde | ChEBI | | 2-Methoxy-4-formylphenol | HMDB | | 4-Hydroxy 3-methoxybenzaldehyde | HMDB | | 4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillin | HMDB | | 4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0) | HMDB | | 4-Hydroxy-5-methoxybenzaldehyde | HMDB | | Lioxin | HMDB | | m-Methoxy-p-hydroxybenzaldehyde | HMDB | | Methyl-protocatechualdehyde | HMDB | | Methylprotcatechuic aldehyde | HMDB | | Oleo-resins vanilla | HMDB | | Oleo-resins vanilla-bean | HMDB | | Oleoresin vanilla | HMDB | | Propenylguaethol | HMDB | | Protocatechualdehyde 3-methyl ether | HMDB | | trans-2-Ethoxy-5-(1-propenyl)phenol | HMDB | | Vanilin | HMDB | | Vanilla | HMDB | | Vanilla oleoresin | HMDB | | Vanillin (3-methoxy-4-hydroxy- benzaldehyde) | HMDB | | Vanillin (natural) | HMDB | | Vanillin (NF) | HMDB | | Vanillin sodium salt | HMDB | | Vanilline | HMDB | | Zimco | HMDB | | Vanillin, sodium salt | HMDB | | 5-Bromovanillin | HMDB | | 5-Chlorovanillin | HMDB | | 4-Hydroxy-3-methoxy-benzyldehyde | PhytoBank | | Vanillum | PhytoBank |
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| Chemical Formula | C8H8O3 |
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| Average Mass | 152.1473 Da |
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| Monoisotopic Mass | 152.04734 Da |
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| IUPAC Name | 4-hydroxy-3-methoxybenzaldehyde |
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| Traditional Name | vanillin |
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| CAS Registry Number | 121-33-5 |
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| SMILES | COC1=CC(C=O)=CC=C1O |
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| InChI Identifier | InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 |
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| InChI Key | MWOOGOJBHIARFG-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol, simulated) | Jtkp6n | Sumner Lab, University of Missouri | Jay Koller | 2022-07-05 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, CD3OD, experimental) | hxkuang@hljucm.net | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | sumnerlw@missouri.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | | TOCSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | jtkp6n@mail.missouri.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | jtkp6n@mail.missouri.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | jtkp6n@mail.missouri.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | jtkp6n@mail.missouri.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-10 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-10 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-10 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-01-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, simulated) | Not Available | Not Available | Not Available | 2024-05-11 | View Spectrum |
| | 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 methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenols |
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| Sub Class | Methoxyphenols |
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| Direct Parent | Methoxyphenols |
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| Alternative Parents | |
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| Substituents | - Methoxyphenol
- Hydroxybenzaldehyde
- Anisole
- Benzaldehyde
- Benzoyl
- Phenoxy compound
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- Aryl-aldehyde
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Ether
- Organooxygen compound
- Aldehyde
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 81.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 11 mg/mL at 25 °C | Not Available | | LogP | 1.21 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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