20665-85-4

Basic information

• Product Name: Vanillin isobutyrate
• Synonyms: 3-Methoxy-4-(2-methylpropanoyloxy)benzaldehyde;Isobutyric acid 2-methoxy-4-formylphenyl ester;2-methyl-propanoic acid 4-formyl-2-methoxyphenylester;4-formyl-2-methoxyphenyl 2-methylpropanoate;4-ISOBUTYRATE-3-METHOXYBENZALDEHYDE;4-formyl-2-methoxyphenyl isobutyrate;ISOBUTAVAN;ISOBUTYL LIGNATE
• CAS NO: 20665-85-4
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• EINECS: 243-956-6
• Product Categories: Alphabetical Listings;Flavors and Fragrances;Q-Z
• Mol File: 20665-85-4.mol

Chemical Properties

• Melting Point: 27.0 to 31.0 °C
• Boiling Point: 312.938 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Almost colourless liquid
• Density: 1.12 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Solubility: soluble in Methanol
• Water Solubility: 573mg/L at 20℃
• CAS DataBase Reference: Vanillin isobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Vanillin isobutyrate(20665-85-4)
• EPA Substance Registry System: Vanillin isobutyrate(20665-85-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 20665-85-4(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Vanillin isobutyrate is used as a flavoring agent for creating floral, caramel, and vanilla flavors. Its unique creamy and sweet characteristics make it a valuable ingredient in the formulation of various food and beverage products.
Used in Fragrance Industry:
Vanillin isobutyrate is used as a fragrance ingredient in the creation of white soap fragrances. Its less discolorizing property allows it to be used at higher levels, up to 2%, without causing significant color changes. This makes it a preferred choice for formulations that require a creamy and sweet scent.
Used in Pharmaceutical Industry:
Vanillin isobutyrate can be used as a pharmaceutical excipient, particularly in the formulation of oral and topical medications. Its creamy and sweet characteristics can enhance the sensory experience of the medication, making it more palatable for patients.
Used in Cosmetic Industry:
Vanillin isobutyrate can be used as a cosmetic ingredient, particularly in the formulation of creams, lotions, and other skincare products. Its creamy and sweet scent can provide a pleasant sensory experience for users, while its less discolorizing property ensures that it does not affect the product's appearance.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Odor at 1.0%

InChI:InChI=1/C12H14O4/c1-8(2)12(14)16-10-5-4-9(7-13)6-11(10)15-3/h4-8H,1-3H3

Upstream product

• 121-33-5 vanillin 
• 79-31-2 isobutyric Acid 
• 97-72-3 2-Methylpropionic anhydride 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 452363-07-4 C₂₁H₁₈O₅ 
• 1417183-19-7 C₂₀H₂₃NO₄*ClH 
• 1417182-32-1 C₂₀H₂₃NO₄ 
• 1314034-84-8 2-(4-isobutyryloxy-3-methoxyphenyl)-5-methyl-1H-benzimidazole 
• 1198406-26-6 C₂₄H₂₃NO₃ 
• 1198407-09-8 C₂₄H₂₅NO₃ 
• 1254182-05-2 C₄₂H₅₀N₂O₇ 
• 1289424-18-5 methyl (E,S)-2-(4-isobutyryloxy-3-methoxybenzylideneamino)-3-phenylpropionate 
• 1236308-45-4 methyl (E,S)-2-(4-isobutyryloxy-3-methoxybenzylideneamino)-3-methylbutyrate 
• 1223077-33-5 C₃₀H₂₈N₄O₃ 
• 1211396-24-5 2-methoxy-4-[(E)-4-phenoxyphenyliminomethyl]phenyl 2-methylpropanoate 
• 1215097-76-9 4-[(E)-hexadecyliminomethyl]-2-methoxyphenyl 2-methylpropanoate 

Relevant articles and documents

Molecular dynamics simulation, synthesis and topoisomerase inhibitory actions of vanillin derivatives: a systematic computational structural integument

A series of 4-hydroxy-3-methoxy benzaldehyde (vanillin) derivatives (3a–3r) was designed for the principle of Schiff base condensation with several individual sulfanilamide analogues. The inhibitory potencies of the designed compounds were evaluated through molecular docking simulation studies against the targets, breast cancer-topo isomerase-IIα and estrogen receptor-α; and the top scoring poses with higher binding energy were selected to assess the mode of binding and stability of each complex through molecular dynamics simulations. Compounds that remained stable in the active sites of the both target receptors through a number of strong H-bonds and hydrophobic contacts were selected. Based on the computational results, these selected compounds, 3b, 3e and 3f were synthesized and were followed up for structural elucidation attempts, by FT/ATR, 1H NMR and 13C NMR. From the experimental in vitro studies on 3b, 3e and 3f, the following remarkable activities against breast cancer cell line were done; IC50 values of 3b, 3e and 3f were noted, 6.7, 4.3 and 11 ng/mL, respectively. These newly synthesized compounds may be used as novel inhibitors of nuclear receptors with potential therapeutic applications in control of cancer. Communicated by Ramaswamy H. Sarma.

Vanillin esters in reactions with indan-1,3-dione

2-Methoxy-4-(12-oxo-12H-benzo[f]indeno[1,2-b]quinolin-13-yl)phenyl esters of carboxylic acids were synthesized by the three component condensation of indan-1,3-dione, 2-naphthylamine, and O-acylvanillin. 2-Arylidenindan-1,3-diones formed during the reaction were isolated. Springer Science+Business Media, Inc. 2006.

Preparative synthesis of vanillin and vanillal alkanoates

Procedures for preparing vanillin and vanillal alkanoates were developed.

Vanilline alkanoates in the synthesis of hexahydrobenzacridine and octahydroxanthene derivatives

Cascade heterocyclization of 1,3-cyclohexanedione and dimedone with 2-naphthylamine and vanilline esters gave derivatives of 2-methoxy-4-(alkyl-11- oxo-7,8,9,10,11,12-hexahydrobenz[a]acridin-12-yl)- and 2-methoxy-4-(alkyl-1,8- dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl esters of aliphatic (C1- C4 ) carboxylic acids. 2005 Pleiades Publishing, Inc.

Vanillin esters of aliphatic acids in the synthesis of 4,7-phenanthroline derivatives

Condensation of vanillin esters of aliphatic acids with 6-aminoquinoline and cyclic c-diketones (1,3-cyclohexanedione and dimedone) afforded new 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl) phenyl esters of carboxylic acids.

1'-Hydroxyeugenol- and coniferyl alcohol derivatives as effective inhibitors of 5-lipoxygenase and Cu(2+)-mediated low density lipoprotein oxidation. Evidence for a dual mechanism.

1'-Hydroxyeugenol- and epoxy-Z-coniferyl alcohol esters from Coreopsis species as well as synthetic derivatives of these natural compounds were examined as lipoxygenase inhibitors and as LDL (low density lipoprotein)-stabilizing agents. Most of the compounds displayed inhibitory activity on the formation of leukotrienes (LTB4 and LTC4) in a cellular (RBL-1 cells) assay as well as in a cell-free 5-lipoxygenase assay at concentrations of 4-24 mumol/l. No effect of selected compounds was observed on mammalian lipoxygenases with other specificity (12- and 15-lipoxygenase). The more lipophilic derivatives also effectively reduced Cu(2+)-mediated oxidation of LDL. The findings are discussed on the base of structure-activity relationships.