Highly selective synthesis of menthols from citral in a one-step process

Trasarti, Andrés Fernando; Marchi, Alberto J.; Apesteguı́a, C.R.

doi:10.1016/j.jcat.2004.03.016

Cited by 79 publications

(62 citation statements)

References 8 publications

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“…Citronellal has a strong aroma of green citrus and a mild smell of woody, which is widely used in fragrance industry (Lenardao et al 2007). Comparing to (S)-enantiomer, (R)-citronellal is more valuable, and it is a particularly useful intermediate for the synthesis of l-menthol, one of the world's largest flavoring chemicals (Trasarti et al 2004). …”

Section: Introductionmentioning

confidence: 99%

Identification of a yeast old yellow enzyme for highly enantioselective reduction of citral isomers to (R)-citronellal

Zheng

Lin

Zhang

et al. 2018

Bioresour. Bioprocess.

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Background: A NAD(P)H-dependent enoate reductase (OYE2p) from Saccharomyces cerevisiae YJM1341 was discovered by genome data mining for asymmetric reduction of (E/Z)-citral to (R)-citronellal with high enantioselectivity. Methods:This enzyme was heterologously expressed in E. coli and characterized for its biocatalytic properties. OYE2p was identified with reduction activities toward a diverse range of ɑ,β-unsaturated compounds bearing conjugated aldehyde, ketone, imide, carboxylic acid and ester.Results: OYE2p showed the highest specific activity at 40 °C and a pH optimum at 7.0-8.0. The stability of OYE2p was rather pH-independent, and the half-life time values of the enzyme at pH 6.0-8.0 were more than 257 h. With regard to the reduction of (E)-citral and (Z)-citral, OYE2p exhibited different selectivity patterns. (E)-citral was exclusively reduced to (R)-citronellal by OYE2p in ≥ 99% ee, which was independent on pH. OYE2p produced both enantiomers of citronellal from (Z)-citral, but showed (R)-citronellal formation tendency, and the ee value of (R)-citronellal was affected by pH in the reaction system. Accordingly, the ee values for (R)-citronellal formation increased with the increasing levels of E-isomer in the (E/Z)-citral mixture as well as the increase of pH. Under the reaction conditions (30 °C and pH 8.6), using purified OYE2p as catalyst, 200 mM (E/Z)-citral (an approximately 10:9 mixture of geometric E-isomer and Z-isomer) was efficiently converted to (R)-citronellal with 88.8% ee and 87.2% yield. Conclusion:All these positive features demonstrate high potential of OYE2p for practical synthesis of (R)-citronellal and in asymmetric reduction of activated alkenes.

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Section: Introductionmentioning

confidence: 99%

Identification of a yeast old yellow enzyme for highly enantioselective reduction of citral isomers to (R)-citronellal

Zheng

Lin

Zhang

et al. 2018

Bioresour. Bioprocess.

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“…23,24 Later reports described the use of Pt/H-beta zeolites 25 and Pd-heteropolyacids 26 for the same reaction of menthol synthesis from citronellal, or even starting from citral, which requires an additional hydrogenation step. 27,28 These are excellent examples of catalysts based on supported metal nanoparticles in which the support not only affords a medium for dispersing the metal nanoparticles, but it does also participate actively in the catalytic process. In that sense, the high surface areas and pore volumes characteristic of some MOFs, make them excellent candidates for attaining high dispersion of metal nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

MOFs as multifunctional catalysts: One-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst

2012

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“…Minyak kemangi banyak digunakan sebagai flavoring agen, minyak kemangi juga digunakan untuk campuran parfum dan pewangi sabun. Senyawa sitral memiliki potensi yang besar untuk dikonversi menjadi senyawa-senyawa terpenoid lainnya yang bermanfaat [5], [6] . Senyawa sitral merupakan senyawa yang memiliki isomer geometris yaitu trans-sitral dan cissitral.…”

Section: Pendahuluanunclassified

Isolation of CIS- And Trans-Sitrals from Basil Essential Oil (Ocimum Citriodorum, L) with Bisulfit Extraction Method and Steam Distillation Method

Rubiyanto

Fitriyah

2016

IJEO

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Abstrak Telah dilakukan penelitian secara eksperimen laboratorium tentang isolasi sitral yang merupakan komponen terbesar dari minyak kemangi (Ocimum citriodorum, L). Minyak kemangi dapat diisolasi dari tanaman kemangi dengan penyulingan uap (steam distillation Abstract Has conducted research in laboratory experiments on isolation sitral which is the largest component of oil of basil (Ocimum citriodorum, L). Basil oil can be isolated from the basil plant with steam distillation (steam distillation

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Highly selective synthesis of menthols from citral in a one-step process

Cited by 79 publications

References 8 publications

Identification of a yeast old yellow enzyme for highly enantioselective reduction of citral isomers to (R)-citronellal

Identification of a yeast old yellow enzyme for highly enantioselective reduction of citral isomers to (R)-citronellal

MOFs as multifunctional catalysts: One-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst

Isolation of CIS- And Trans-Sitrals from Basil Essential Oil (Ocimum Citriodorum, L) with Bisulfit Extraction Method and Steam Distillation Method

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