96503-29-6

Usage

Uses

Used in Food and Beverage Industry:
(S)-2-Hydroxy-propionaldehyde dimethoxyacetal is used as a flavoring agent for its distinctive sweet and fruity aroma, enhancing the taste and smell of various food and beverage products.
Used in Perfumery and Fragrance Industry:
(S)-2-HYDROXY-PROPIONALDEHYDE DIMETHOXYACETAL serves as a fragrance ingredient, contributing to the creation of unique and appealing scents in perfumes and other fragranced products.
Used in Cosmetics and Personal Care Products:
(S)-2-Hydroxy-propionaldehyde dimethoxyacetal is utilized in the formulation of cosmetics and personal care products for its pleasant odor, improving the sensory experience for consumers.

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 6342-56-9 Pyruvic aldehyde dimethyl acetal 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 13031-04-4 ketopantolactone 
• 6175-45-7 2,2-diethoxyacetophenone 

Downstream Products

• 598-35-6 L-lactaldehyde 

Relevant academic research and scientific papers

Heterogeneous enantioselective hydrogenation in a continuousflow fixed-bed reactor system: Hydrogenation of activated ketones and their binary mixtures on pt-alumina-cinchona alkaloid catalysts

Under the experimental conditions of the Orito reaction the individual hydrogenation and the competitive hydrogenations of three binary mixtures of methyl benzoylformate (MBF), pyruvic aldehyde dimethyl acetal (PA) and 2,2-diethoxyacetophenone (DAP) on platinum-alumina catalysts modified by cinchonidine, cinchonine, quinine and quinidine (Pt-CD, Pt-CN, Pt-QN, Pt-QD) were studied for the first time using continuous-flow fixed-bed reactor system. Conversions of chiral (Cc) and racemic (Cr) hydrogenations of all three compounds and enantioselectivities (ee) were determined under the same experimental conditions (under 4 MPa H2 pressure, at room temperature using toluene/AcOH 9/1 as solvent).The order of the rates of the enantioselective hydrogenations of the three substrates studied is MBF > PA > DAP, and the order of their ee values is MBF ? PA > DAP. The hydrogenation rate and the effect of rate on ee depend on the structure of the cinchona used: hydrogenation of MBF and PA may produce ee values over 90 %, however, the ee values were conspicuously low in the presence of Pt-QN and especially of Pt-QD catalysts. In the chiral hydrogenation of DAP considering racemic hydrogenation rate decrease (Cc/Cr 1) takes place instead of rate enhancement over all four catalysts. The new experimental data supported the so far known fundamental rules of the Orito reaction based on batch studies. Springer Science+Business Media, LLC 2012.

New phenomenon in competitive hydrogenation of binary mixtures of activated ketones over unmodified and cinchonidine-modified Pt/alumina catalyst

Competitive hydrogenations of eight binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), ketopantolactone (KPL), pyruvic aldehyde dimethyl acetal (PA) and trifluoroacetophenone (TFAP) on platinum/alumina catalysts unmodified (racemic hydrogenation) and modified by cinchonidine (chiral hydrogenation) were studied under the experimental conditions of the Orito reaction. Reaction rates of chiral and racemic hydrogenations were determined and relative adsorption coefficients were calculated. In the competitive chiral hydrogenation of EP + MBF, EP + TFAP and KPL + MBF binary mixtures a new phenomenon was observed: namely the EP and KPL are hydrogenated faster than MBF and TFAP, whereas in racemic one the MBF and TFAP are hydrogenated faster than EP or KPL. Effects of the activated ketones structure on their reactivity and the stability of the surface complexes are discussed. It was found that differences in rate enhancement are caused by the differences both in the adsorptivity and in the reactivity of adsorbed substrates and adsorbed intermediate complexes.

The first case of competitive heterogeneously catalyzed hydrogenation using continuous-flow fixed-bed reactor system: Hydrogenation of binary mixtures of activated ketones on Pt-alumina and on Pt-alumina-cinchonidine catalysts

Under the experimental conditions of the Orito reaction the competitive hydrogenations of four binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), pyruvic aldehyde dimethyl acetal (PA) and 2,2-diethoxyacetophenone (DAP) on unmodified Pt/Al2O3 (racemic hydrogenation) and catalyst modified by cinchonidine (chiral hydrogenation) were studied using continuous-flow fixed-bed reactor system (CFBR). Conversions of chiral and racemic hydrogenations were determined under 4 MPa H2 pressure, at 293 K using toluene/acetic acid 9/1 as solvent. In the competitive chiral hydrogenation of MBF + EP and DAP + PA binary mixtures (S1 + S2) a new phenomenon was observed: namely the EP and PA are hydrogenated faster than MBF and DAP, whereas in racemic one the MBF and DAP are hydrogenated faster than the former ketones. The phenomenon verified for the first time in CFBR is dependent on the adsorption mode of the surface complexes of various compositions (S1-Pt, S2-Pt, S1-CD-Pt, S2-CD-Pt, CD = cinchonidine). In the chiral hydrogenation of DAP a rate decrease, i.e., "ligand deceleration" was observed instead of rate enhancement. Graphical Abstract: [Figure not available: see fulltext.]