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Chemical Structure| 121-33-5 Chemical Structure| 121-33-5
Chemical Structure| 121-33-5

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Vanillin, 4-hydroxy-3-methoxybenzaldehyde, is a food additive, and a modulator candidate for renal injury induced by cisplatin in experimental rats.

Synonyms: p-Vanillin; m-Methoxy-p-hydroxybenzaldehyde; NSC 48383

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Product Citations      Show More

Gendron, David ; Labrecque, Josée ;

Abstract: This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (1H), carbon (13C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) NMR, as well as high-resolution mass spectroscopy (HRMS). We also investigated the optical properties through UV-visible spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. At last, the thermal properties of this divanillin derivative were evaluated by thermogravimetric analysis (TGA) as well as differential scanning calorimetry (DSC).

Keywords: vanillin ; biosourced ; Knoevenagel condensation ; dyes ; organic pigments

Purchased from AmBeed: ;

James D. Sitter ; Tyler Richardson ; Jean M. Wallace ; Clair Lusk ; Loren C. Brown ; Matthew Laskoski

Abstract: The renewable and biosynthetic molecule, , were used in the preparation of new (PN) and (EB) bifunctional resins without pre-modification of the structure. This PN resin was characterized by differential scanning calorimetry, thermogravimetric analysis, nuclear magnetic resonance spectroscopy, rheometry, and single crystal x-ray diffraction. The monomers exhibited excellent rheometric viscosities below 250 Cp at processing temperatures and a good pot life. After complete curing, the PN polymers exhibited thermal stability above 500℃, a glass transition temperature (Tg) above the final postcure temperature of 380℃, and exceptional retention of structural integrity over a large temperature range. These results suggest that derived EBPN based resins are excellent candidates for use in a variety of applications where high temperature and mechanical stability is critical.

Keywords: biopolymers and renewable polymers ; resins ; thermosets

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Product Details of Vanillin

CAS No. :121-33-5
Formula : C8H8O3
M.W : 152.15
SMILES Code : C1=C(OC)C(=CC=C1C=O)O
Synonyms :
p-Vanillin; m-Methoxy-p-hydroxybenzaldehyde; NSC 48383
MDL No. :MFCD00006942
InChI Key :MWOOGOJBHIARFG-UHFFFAOYSA-N
Pubchem ID :1183

Safety of Vanillin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319-H412
Precautionary Statements:P273-P305+P351+P338

Application In Synthesis of Vanillin

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 121-33-5 ]
  • Downstream synthetic route of [ 121-33-5 ]

[ 121-33-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 121-33-5 ]
  • [ 2426-59-7 ]
References: [1] Patent: US2016/9706, 2016, A1, .
  • 2
  • [ 121-33-5 ]
  • [ 27113-22-0 ]
References: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1972, p. 3001 - 3006.
  • 3
  • [ 821-55-6 ]
  • [ 121-33-5 ]
  • [ 27113-22-0 ]
References: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9821 - 9837.
  • 4
  • [ 121-33-5 ]
  • [ 73635-75-3 ]
References: [1] Journal of Materials Chemistry A, 2018, vol. 6, # 15, p. 6667 - 6674.
  • 5
  • [ 121-33-5 ]
  • [ 79-07-2 ]
  • [ 186685-89-2 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In N,N-dimethyl-formamide; acetonitrileReflux General procedure: A mixture of the corresponding halide (0.010 mol), hydroxybenzaldehyde (0.011 mol), and potassium carbonate (2.00 g, 0.0145 mol) in a mixture of acetonitrile-DMF (20 mL, 8 : 2, v/v) was refluxed for 5-7 h with stirring (TLC monitoring). After evaporation of the solvents, the residue was treated with water, a precipitate formed was filtered off, washed with 30percent aqueous methanol, and dried in air. Yields and physicochemical characteristics of aldehydes 9-12 are given in Table 4.
References: [1] Russian Chemical Bulletin, 2015, vol. 64, # 2, p. 395 - 404[2] Izv. Akad. Nauk, Ser. Khim., 2015, # 2, p. 395 - 404,10.
[3] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124.
[4] European Journal of Medicinal Chemistry, 2014, vol. 81, p. 1 - 14.
 

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