26549-25-7

Basic information

• Product Name: 3-Heptanol, (S)-
• CAS NO: 26549-25-7
• Molecular Formula: C7H16O
• Molecular Weight: 116.203
• Mol File: 26549-25-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-Heptanol, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Heptanol, (S)-(26549-25-7)
• EPA Substance Registry System: 3-Heptanol, (S)-(26549-25-7)

Safety Data

• Hazardous Substances Data: 26549-25-7(Hazardous Substances Data)

Upstream product

• 589-82-2 heptan-3-ol 
• 142-82-5 n-heptane 

Downstream Products

• 3525-25-5 (3S)-3-Ethylheptan-1-ol 
• 1974-05-6 (-)(R)-3-bromo-heptane 

Relevant articles and documents

Biocatalytic Racemization Employing TeSADH: Substrate Scope and Organic Solvent Compatibility for Dynamic Kinetic Resolution

Racemization in combination with a kinetic resolution is the base for a dynamic kinetic resolution (DKR). Biocatalytic racemization was successfully performed for a broad scope of sec-alcohols by employing a single alcohol dehydrogenase (ADH) variant from Thermoanaerobacter pseudoethanolicus (formerly T. ethanolicus; TeSADH W110A I86A C295A). The catalyst employed as a lyophilized whole cell preparation or cell free extract, which tolerated various non-water miscible organic solvents under micro-aqueous or two-phase conditions, whereby cyclohexane and n-hexane suited best. Various concepts for combining the enzymatic racemization with an enzymatic kinetic resolution to achieve overall a bis-enzymatic DKR were evaluated. A proof of concept showed a successful DKR with racemization in aqueous phase combined with acylation in the organic phase.

In vitro double oxidation of n-heptane with direct cofactor regeneration

A novel concept for the direct oxidation of cycloalkanes to the corresponding cyclic ketones in a one-pot synthesis in water with molecular oxygen as sole oxidizing agent was reported recently. Based on this concept we have developed a new strategy for the double oxidation of n-heptane to enable a biocatalytic resolution for the direct synthesis of heptanone and (R)-heptanols in a one-pot reaction. The bicatalytic cascade employs an NADH driven P450 BM3 monooxygenase variant (WTNADH, 19A12NADH or CM1 NADH) and an (S)-enantioselective alcohol dehydrogenase (RE-ADH). In the initial step n-heptane is hydroxylated under consumption of NADH to produce (R/S)-heptanol. In the second oxidation step the (S)-heptanol enantiomers are transformed to the corresponding ketones, reducing and thereby regenerating the cofactor. Characterization of initial hydroxylation step revealed high turnover frequencies (TOF) of up to 600 min-1, as well as high coupling efficiencies using NADH as cofactor (up to 44%). In the cascade reaction a nearly 2-fold improved product formation was achieved, compared to the single hydroxylation reaction. The total product concentration reached 1.1 mM, corresponding to a total turnover number (TTN) of 2500. Implementation of an additional cofactor regeneration system (D-glucose/glucose dehydrogenase) enabled a further enhancement in product formation with a total product concentration of 1.8 mM and a TTN of 3500. Copyright