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20296-29-1

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20296-29-1 Usage

Synthesis Reference(s)

Tetrahedron Letters, 18, p. 3407, 1977 DOI: 10.1016/S0040-4039(01)83252-4

Check Digit Verification of cas no

The CAS Registry Mumber 20296-29-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,2,9 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 20296-29:
(7*2)+(6*0)+(5*2)+(4*9)+(3*6)+(2*2)+(1*9)=91
91 % 10 = 1
So 20296-29-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H18O/c1-3-5-6-7-8(9)4-2/h8-9H,3-7H2,1-2H3/t8-/m0/s1

20296-29-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-OCTANOL

1.2 Other means of identification

Product number -
Other names OCTANOL,3

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20296-29-1 SDS

20296-29-1Relevant academic research and scientific papers

1,1′-Binaphthyl-2,2′-diyl phosphoroselenoyl chloride as a chiral molecular tool for the preparation of enantiomerically pure alcohols and amines

Murai, Toshiaki,Matsuoka, Daichi,Morishita, Ken

, p. 4584 - 4585 (2006)

Enantiomerically pure phosphoroselenoyl chloride bearing a binaphthyl group was synthesized. This phosphoroselenoyl chloride was used to discriminate and resolve simple secondary alcohols. Stereospecific conversions of diastereomerically pure phosphoroselenoic acid esters, obtained by reaction of the chloride with simple secondary alcohols, to enantiomerically pure alcohols and amines were also achieved. Copyright

Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

Garcia, Jordi,Lopez, Marta,Romeu, Joan

, p. 2617 - 2626 (1999)

The first stereoselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn- 3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)- 19-methyl-1-trimethylsilylicos- 4-en-1-yn-3-one in the presence of a chiral oxazaborolidine.

Selectivity-enhancement in enantioselective hydrolysis of sec-alkyl sulfates by an alkylsulfatase from Rhodococcus ruber DSM 44541

Pogorevc, Mateja,Strauss, Ulrike T.,Riermeier, Thomas,Faber, Kurt

, p. 1443 - 1447 (2002)

The Enantioselectivity of the biohydrolysis of sec-alkyl sulfate esters using a bacterial alkylsulfatase from Rhodococcus ruber DSM 44541 was dramatically enhanced in presence of additives ('enhancers') such as carbohydrates, polyethylene glycol, detergents, metal ions and through enzyme immobilization. In presence of iron, the E value for the kinetic resolution of (±)-3- and (±)-4-octyl sulfate was improved from E=3.9 to ≥200 and E=1.1 to 10, respectively.

Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1- naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid

Ichikawa, Akio,Ono, Hiroshi

, p. 2559 - 2568 (2005)

Enantioresolution of 3-octanol, 6-methyl-5-hepten-2-ol (sulcatol), and 1-octen-3-ol was conducted using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid) and (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid). In each case, the diastereomeric esters obtained were readily separated by HPLC. The stereochemistry of the esters could be assigned from their respective 1H NMR analyses. Solvolyses of the esters gave enantiopure alcohols and acids. MαNP and M9PP acids displayed almost equivalent properties in 1H NMR anisotropy. The chiral resolving ability of M9PP acid was slightly superior to that of MαNP acid in HPLC.

Enzymatic synthesis of (S)-(-)-1-(2-thienyl)propyl acetate

Kang,Jeon,Yamaguchi,Kim,Ko

, p. 2139 - 2142 (1995)

(±)-1-(2-thienyl)propyl acetate was resolved by PCL (Pseudomonas cepacia lipase) catalyzed hydrolysis to afford (S)-(-)-1-(2-thienyl)propyl acetate in >99% e.e. (S)-(-)-1-(2-thienyl)propyl acetate thus obtained was transformed to (S)-(+)-3-octanol, the alarm pheromone of ants, Crematogaster castanea and liengmei.

Chemoenzymatic synthesis of α-halogeno-3-octanol and 4- or 5-nonanols. Application to the preparation of chiral epoxides

Besse, Pascale,Sokoltchik, Tania,Veschambre, Henri

, p. 4441 - 4457 (1998)

A study of the microbiological reduction of different α- halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides.

Organic-inorganic nanocrystal reductase to promote green asymmetric synthesis

Koesoema, Afifa Ayu,Matsuda, Tomoko,Tsriwong, Kotchakorn

, p. 30953 - 30960 (2020/09/11)

An acetophenone reductase from Geotrichum candidum (GcAPRD) was immobilized by the organic-inorganic nanocrystal method. The GcAPRD nanocrystal presented improved stability and recyclability compared with those of the free GcAPRD. Moreover, the GcAPRD nanocrystal reduced broad kinds of ketones with excellent enantioselectivities to produce beneficial chiral alcohols such as (S)-1-(3′,4′-dichlorophenyl)ethanol with >99% yield and >99% ee. The robust and versatile properties of the GcAPRD nanocrystal demonstrated an approach to promote green asymmetric synthesis and sustainable chemistry. This journal is

Structural basis for a highly (S)-enantioselective reductase towards aliphatic ketones with only one carbon difference between side chain

Koesoema, Afifa Ayu,Sugiyama, Yosuke,Xu, Zichang,Standley, Daron M.,Senda, Miki,Senda, Toshiya,Matsuda, Tomoko

, p. 9543 - 9553 (2019/09/16)

Aliphatic ketones, such as 2-butanone and 3-hexanone, with only one carbon difference among side chains adjacent to the carbonyl carbon are difficult to be reduced enantioselectively. In this study, we utilized an acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD) to reduce challenging aliphatic ketones such as 2-butanone (methyl ethyl ketone) and 3-hexanone (ethyl propyl ketone) to their corresponding (S)-alcohols with 94% ee and > 99% ee, respectively. Through crystallographic structure determination, it was suggested that residue Trp288 limit the size of the small binding pocket. Docking simulations imply that Trp288 plays an important role to form a C-H?π interaction for proper orientation of ketones in the pro-S binding pose in order to produce (S)-alcohols. The excellent (S)-enantioselectivity is due to a non-productive pro-R binding pose, consistent with the observation that the (R)-alcohol acts as an inhibitor of (S)-alcohol oxidation.

Photostable Helical Polyfurans

Varni, Anthony J.,Fortney, Andria,Baker, Matthew A.,Worch, Joshua C.,Qiu, Yunyan,Yaron, David,Bernhard, Stefan,Noonan, Kevin J. T.,Kowalewski, Tomasz

supporting information, p. 8858 - 8867 (2019/06/07)

This report describes the design and synthesis of a new class of polyfurans bearing ester side chains. The macromolecules can be synthesized using catalyst-transfer polycondensation, providing precise control over molecular weight and molecular weight distribution. Such obtained furan ester polymers are significantly more photostable than their alkyl analogues owing to the electron-withdrawing nature of the attached subunit. Most interestingly, they spontaneously fold into a compact π-stacked helix, yielding a complex multilayer cylindrical nanoparticle with a hollow, rigid, conjugated core composed of the polyfuran backbone and a soft, insulating outer layer formed by the ester side chains. The length of polymer side chains dictates the outer diameter of such nanoparticles, which for the hexyl ester groups used in the present study is equal to ~2.3 nm. The inner cavity of the conjugated core is lined with oxygen atoms, which set its effective diameter to 0.4 nm. Furthermore, installation of bulkier, branched chiral ester side chains on the repeat unit yields structures that, upon change of solvent, can reversibly transition between an ordered chiral helical folded and disordered unfolded state.

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Demming, Rebecca M.,Hammer, Stephan C.,Nestl, Bettina M.,Gergel, Sebastian,Fademrecht, Silvia,Pleiss, Jürgen,Hauer, Bernhard

supporting information, p. 173 - 177 (2018/12/11)

The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long-standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.

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