68527-74-2

Basic information

• Product Name: VANILLIN PROPYLENE GLYCOL ACETAL
• Synonyms: 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)-pheno;FEMA 3905;VANILLIN PROPYLENE GLYCOL ACETAL;Vanilline Propylene Glycol Acetal;2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol;Phenol,2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl);VANILLINEPROPYLENEGLYCOLACETATE;VANILLIN PROPYLENE GLYCOL ACETAL 75% TECH. GRADE
• CAS NO: 68527-74-2
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• EINECS: 271-279-6
• Mol File: 68527-74-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 333.1 °C at 760 mmHg
• Flash Point: 155.3 °C
• Appearance: /
• Density: 1.184 g/cm³
• Vapor Pressure: 7.21E-05mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: 2-8°C
• PKA: 9.80±0.35(Predicted)
• CAS DataBase Reference: VANILLIN PROPYLENE GLYCOL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: VANILLIN PROPYLENE GLYCOL ACETAL(68527-74-2)
• EPA Substance Registry System: VANILLIN PROPYLENE GLYCOL ACETAL(68527-74-2)

Safety Data

• Hazardous Substances Data: 68527-74-2(Hazardous Substances Data)

Usage

Uses

Vanillin Propylene Glycol Acetal as a flavoring agent. Has similar taste and smell as Vanillin(V097500).

InChI:InChI=1/C11H14O4/c1-7-6-14-11(15-7)8-3-4-9(12)10(5-8)13-2/h3-5,7,11-12H,6H2,1-2H3

Synthetic route

vanillin (121-33-5) + 3-monochloro-1,2-propanediol (96-24-2) → 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol (68527-74-2)

Conditions	Yield
With FIBAN K-1 cation exchanger In benzene Dean-Stark; Reflux;	89%

propylene glycol (57-55-6) + vanillin (121-33-5) → 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol (68527-74-2)

Conditions	Yield
With Sn-TUD-1 mesoporous silicates In toluene at 115℃; Reagent/catalyst; Dean-Stark;
With Al-ITQ-SO3H In toluene at 90℃; Dean-Stark; Inert atmosphere;

1-Adamantanecarbonyl chloride (2094-72-6) + 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol (68527-74-2) → 2-methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenyl 1-adamantanecarboxylate

Conditions	Yield
With pyridine In benzene for 8h; Heating;	72%

Upstream product

• 57-55-6 propylene glycol 
• 121-33-5 vanillin 
• 96-24-2 3-monochloro-1,2-propanediol 

Relevant articles and documents

MOFs based on 1D structural sub-domains with Br?nsted acid and redox active sites as effective bi-functional catalysts

A novel family of lamellar MOF-type materials, which contain Br?nsted acid sites together with redox active centers, based on assembled 1D organic-inorganic nanoribbons were obtained through direct solvothermal synthesis routes, using specific monotopic benzylcarboxylate spacers with thiol substituents in thepara-position like structural modulator compounds and effective post-synthesis oxidized treatments to generate accessible sulfonic groups. Low-dimensional aluminum metal-organic materials, containing free sulfonic pendant groups (Al-ITQ-SO3H), were successfully tested in several acid reactions, such as acetalization, esterification and ring opening of epoxides with a significant impact on fine chemistry processes. The direct introduction of stabilized Pd nanoparticles, cohabitating with pendant sulfonic groups, allowed the preparation of active bi-functional MOF-type hybrid materials (Al-ITQ-SO3H/Pd) capable of carrying out one-pot two-step oxidation-acetalization reactions, exhibiting high yield and high activity during consecutive catalytic cycles.

Metal-containing TUD-1 mesoporous silicates as versatile solid acid catalysts for the conversion of bio-based compounds into valuable chemicals

Three-dimensional mesoporous silicates of the TUD-1 family were synthesised with different metals (Zr, Hf and Sn) incorporated in the framework of the material. The mesoporosity of the prepared TUD-1s was confirmed by X-ray diffraction (XRD), nitrogen physisorption and TEM. The incorporation of the metals in the silicate structure was investigated by FT-IR and UV-Vis spectroscopy. All three TUD-1 materials present a combination of Lewis and mild Br?nsted acid sites, as determined by TPD-FT-IR of pyridine adsorption. The metal-containing TUD-1 materials were tested as solid acid catalysts for the conversion of three bio-based compounds into valuable chemical products. In the conversion of dihydroxyacetone into ethyl lactate, complete selectivity towards the desired lactate product was achieved with Zr-, Hf- and Sn-TUD-1. The three heterogeneous catalysts displayed similar activity, with Hf-TUD-1 reaching the highest conversion and metal-based turnover number. Sn-TUD-1 also displayed high activity and selectivity in two acetalisation reactions, i.e. the synthesis of solketal from acetone and glycerol and the reaction of vanillin with propylene glycol. The catalytic performance of these TUD-1 materials is ascribed to the high accessibility of their active sites and to the suitable combination of acid sites. The catalysts were successfully reused in consecutive runs and did not suffer from leaching.

Synthesis of 1,3-dioxolanes from substituted benzaldehydes of the vanillin series

Abstract-Condensation of substituted benzaldehydes of the vanillin series with propane-1,2-diol and 3- chloropropane-1,2-diol in boiling benzene in the presence of FIBAN K-1 sulfonated cation exchanger as catalyst gave the corresponding substituted 1,3-di

VANILLIN ACETALS AND SENSORY STIMULANT COMPOSITION CONTAINING THE SAME

The invention relates to a sensory stimulant composition containing one or more of vanillin acetals represented by the general formula (1), and a flavor and fragrance composition, a beverage or food product, a fragrance or cosmetic product, a daily utensil product, an oral composition, or a pharmaceutical product containing the sensory stimulant composition with a warming sensation agent or cooling sensation substance, if necessary. Vanillin acetals represented by the general formula (1) show an excellent pungent and/or warming sensation effect and a cooling sensation-emphasizing effect.