Ortho-Vanillin
Chemical compound From Wikipedia, the free encyclopedia
ortho-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants.[1][2][3] Its functional groups include aldehyde, ether and phenol. ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer, para-vanillin. The "ortho-" prefix refers to the position of the compound’s hydroxyl moiety, which is found in the para-position in vanillin.
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| Names | |
|---|---|
| Preferred IUPAC name
2-Hydroxy-3-methoxybenzaldehyde | |
| Other names
o-Vanillin 3-Methoxysalicylaldehyde | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.197 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H8O3 | |
| Molar mass | 152.15 g/mol |
| Appearance | Yellow, fibrous solid |
| Density | 1.231 g/mL |
| Melting point | 40 to 42 °C (104 to 108 °F; 313 to 315 K) |
| Boiling point | 265 to 266 °C (509 to 511 °F; 538 to 539 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
May cause irritation to skin, eyes, and respiratory tract |
| GHS labelling: | |
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| Danger | |
| H302, H315, H317, H318, H319, H335 | |
| P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
| Flash point | > 110 °C (230 °F; 383 K) |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related compounds |
Eugenol, Anisaldehyde, Phenol, Vanillin |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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ortho-Vanillin is a fibrous, light-yellow, crystalline solid. Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive.
History
ortho-Vanillin was first isolated, in 1876, by renowned German chemist Ferdinand Tiemann.[4] By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins.[5]
By 1920, the compound began to show use as a dye for hides.[6]
Biological properties
ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD50 of 1330 mg/kg in mice.[7]
It is a weak inhibitor of tyrosinase,[8] and displays both antimutagenic and comutagenic properties in Escherichia coli.[9] However, its net effect makes it a “potent comutagen”.[10]
ortho-Vanillin possesses moderate antifungal and antibacterial properties.[11]
Uses
Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals, for example, benafentrine[12] and an antiandrogen compound called Pentomone.
See also
Notes
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