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DIHYDROCARVEOL is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 38049-26-2 Structure
  • Basic information

    1. Product Name: DIHYDROCARVEOL
    2. Synonyms: 1-METHYL-4-ISOPROPENYL-2-CYCLOHEXANOL;CARHYDRANOL;FEMA 2379;DIHYDROCARVEOL;(1.alpha.,2.beta.,5.alpha.)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-ol;2-methyl-5-(1-methylethenyl)-,(1alpha,2beta,5alpha)-cyclohexano;DIHYDROCARVEOL WITH GC;(1R,2R,5R)-2-Methyl-5-(prop-1-en-2-yl)cyclohexanol
    3. CAS NO:38049-26-2
    4. Molecular Formula: C10H18O
    5. Molecular Weight: 154.25
    6. EINECS: 253-755-5
    7. Product Categories: N/A
    8. Mol File: 38049-26-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 224-225 °C(lit.)
    3. Flash Point: 197 °F
    4. Appearance: /
    5. Density: 0.926 g/mL at 25 °C(lit.)
    6. Vapor Density: 5.3 (vs air)
    7. Vapor Pressure: 0.1 mm Hg ( 20 °C)
    8. Refractive Index: n20/D 1.479
    9. Storage Temp.: 2-8°C
    10. Solubility: N/A
    11. PKA: 15.20±0.60(Predicted)
    12. CAS DataBase Reference: DIHYDROCARVEOL(CAS DataBase Reference)
    13. NIST Chemistry Reference: DIHYDROCARVEOL(38049-26-2)
    14. EPA Substance Registry System: DIHYDROCARVEOL(38049-26-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 2
    5. RTECS: OT0175150
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 38049-26-2(Hazardous Substances Data)

38049-26-2 Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 187, 1988 DOI: 10.1021/jo00236a038

Check Digit Verification of cas no

The CAS Registry Mumber 38049-26-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,0,4 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 38049-26:
(7*3)+(6*8)+(5*0)+(4*4)+(3*9)+(2*2)+(1*6)=122
122 % 10 = 2
So 38049-26-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O/c1-8(2)10(3)7-5-4-6-9(10)11/h9,11H,1,4-7H2,2-3H3

38049-26-2Relevant articles and documents

From Bugs to Bioplastics: Total (+)-Dihydrocarvide Biosynthesis by Engineered Escherichia coli

Ascue Avalos, Gabriel A.,Toogood, Helen S.,Tait, Shirley,Messiha, Hanan L.,Scrutton, Nigel S.

, p. 785 - 792 (2019/01/29)

The monoterpenoid lactone derivative (+)-dihydrocarvide ((+)-DHCD) can be polymerised to form shape-memory polymers. Synthetic biology routes from simple, inexpensive carbon sources are an attractive, alternative route over chemical synthesis from (R)-carvone. We have demonstrated a proof-of-principle in vivo approach for the complete biosynthesis of (+)-DHCD from glucose in Escherichia coli (6.6 mg L?1). The pathway is based on the Mentha spicata route to (R)-carvone, with the addition of an ′ene′-reductase and Baeyer–Villiger cyclohexanone monooxygenase. Co-expression with a limonene synthesis pathway enzyme enables complete biocatalytic production within one microbial chassis. (+)-DHCD was successfully produced by screening multiple homologues of the pathway genes, combined with expression optimisation by selective promoter and/or ribosomal binding-site screening. This study demonstrates the potential application of synthetic biology approaches in the development of truly sustainable and renewable bioplastic monomers.

Dihydridoboranes: Selective Reagents for Hydroboration and Hydrodefluorination

Phillips, Nicholas A.,O'hanlon, James,Hooper, Thomas N.,White, Andrew J. P.,Crimmin, Mark R.

supporting information, p. 7289 - 7293 (2019/10/08)

The preparation of a new series of dihydridoboranes supported by N,N-chelating ligands, [R2NCH2CH2NAr]- (R = alkyl, Ar = aryl), is reported. These new boranes react selectively with carbonyls, imines, and a series of electron-deficient fluoroarenes. The reactivity is complementary to recognized reagents such as pinacolborane, catecholborane, NHC-BH3, and borane (BH3) itself. Selectivities are rationalized by invoking both open- A nd closed-chain forms of the reagents as part of equilibrium mixtures.

Stereodivergent Synthesis of Carveol and Dihydrocarveol through Ketoreductases/Ene-Reductases Catalyzed Asymmetric Reduction

Guo, Jiyang,Zhang, Rui,Ouyang, Jingping,Zhang, Feiting,Qin, Fengyu,Liu, Guigao,Zhang, Wenhe,Li, Hengyu,Ji, Xiaohong,Jia, Xian,Qin, Bin,You, Song

, p. 5496 - 5504 (2018/11/30)

Chiral carveol and dihydrocarveol are important additives in the flavor industry and building blocks in the synthesis of natural products. Despite the remarkable progress in asymmetric catalysis, convenient access to all possible stereoisomers of carveol and dihydrocarveol remains a challenge. Here, we present the stereodivergent synthesis of carveol and dihydrocarveol through ketoreductases/ene-reductases catalyzed asymmetric reduction. By directly asymmetric reduction of (R)- and (S)-carvone using ketoreductases, which have Prelog or anti-Prelog stereopreference, all four possible stereoisomers of carveol with medium to high diastereomeric excesses (up to >99 %) were first observed. Then four stereoisomers of dihydrocarvone were prepared through ene-reductases catalyzed diastereoselective synthesis. Asymmetric reduction of obtained dihydrocarvone isomers by ketoreductases further provide access to all eight stereoisomeric dihydrocarveol with up to 95 % de values. In addition, the absolute configurations of dihydrocarveol stereoisomers were determined by using modified Mosher's method.

Production of flavours and fragrances via bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by non-conventional yeast whole-cells

Goretti, Marta,Turchetti, Benedetta,Cramarossa, Maria Rita,Forti, Luca,Buzzini, Pietro

, p. 5736 - 5748 (2013/07/19)

As part of a program aiming at the selection of yeast strains which might be of interest as sources of natural flavours and fragrances, the bioreduction of (4R)-(-)-carvone and (1R)-(-)-myrtenal by whole-cells of non-conventional yeasts (NCYs) belonging to the genera Candida, Cryptococcus, Debaryomyces, Hanseniaspora, Kazachstania, Kluyveromyces, Lindnera, Nakaseomyces, Vanderwaltozyma and Wickerhamomyces was studied. Volatiles produced were sampled by means of headspace solid-phase microextraction (SPME) and the compounds were analysed and identified by gas chromatography-mass spectroscopy (GC-MS). Yields (expressed as % of biotransformation) varied in dependence of the strain. The reduction of both (4R)-(-)-carvone and (1R)-(-)-myrtenal were catalyzed by some ene-reductases (ERs) and/or carbonyl reductases (CRs), which determined the formation of (1R,4R)-dihydrocarvone and (1R)-myrtenol respectively, as main flavouring products. The potential of NCYs as novel whole-cell biocatalysts for selective biotransformation of electron-poor alkenes for producing flavours and fragrances of industrial interest is discussed.

Synthesis of optically active dihydrocarveol via a stepwise or one-pot enzymatic reduction of (R)- and (S)-carvone

Chen, Xi,Gao, Xiuzhen,Wu, Qiaqing,Zhu, Dunming

experimental part, p. 734 - 738 (2012/08/29)

A recombinant enoate reductase LacER from Lactobacillus casei catalyzed the reduction of (R)-carvone and (S)-carvone to give (2R,5R)-dihydrocarvone and (2R,5S)-dihydrocarvone with 99% and 86% de, respectively, which were further reduced to dihydrocarveols by a carbonyl reductase from Sporobolomyces salmonicolor SSCR or Candida magnolia CMCR. For (R)-carvone, (1S,2R,5R)-dihydrocarveol was produced as the sole product with >99% conversion, while (1S,2R,5S)-dihydrocarveol was obtained as the major product, but with a lower de when (S)-carvone was used as the substrate. The one-pot reduction was performed at a 0.1 M substrate concentration, indicating that it might provide an effective synthetic route to this type of chiral compound.

25-Hydroxydihydrotachysterol2. An innovative synthesis of a key metabolite of dihydrotachysterol2

Hanekamp,Rookhuizen,Bos,Brandsma

, p. 9283 - 9294 (2007/10/02)

A new synthesis of 25-hydroxydihydrotachysterol2 is described. The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.

Stereoselective reduction of (R)-(-)-carvone with sodium dithionite in the presence of cyclomaltoheptaose (β-cyclodextrin) and its heptakis(2,6-di-O-methyl) derivative

Fornasier,Marcuzzi,Parmagnani,Tonellato

, p. 245 - 249 (2007/10/02)

The authors have studied the competition between l,4 and l,2-reduction of the conjugated enone (r)-(-)-carvone in the presence of cyclomaltoheptaose and its heptakis derivative using sodium dithionite as a reducing agent in aqueous sodium hydrogen carbonate with or without benzene. The spectrum of products namely the ketones and the alcohols expected from the non-selective reduction of an organic compound is shown.

FUNCTIONALIZED CYCLOPENTANES VIA RADICAL CYCLIZATIONS USING THIOCARBONATE DERIVATIVES AS INITIATORS AND TERMINATORS

Ziegler, Frederick E.,Zheng, Zhong-li

, p. 5973 - 5976 (2007/10/02)

A radical-based cyclization is described that employs xanthates or cyclic thionocarbonates as initiators and allylic dithiocarbonates or allylic thiocarbamates as terminators.

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