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CAS

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114607-20-4

Sitophilate, also known as (-)-Sitophilate or (2S,3R)-Sitophilate, is the enantiomer of the granary weevil aggregation pheromone. It is an optically active compound synthesized using enantioface-selective organoiron complexes as chiral 3-hydroxypropionate-2,3-dication equivalents, demonstrating the potential of this methodology for producing stereochemically defined β-hydroxyesters.

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  • 114607-20-4 Structure

  • Basic information

    1. Product Name: sitophilate
    2. Synonyms: sitophilate
    3. CAS NO:114607-20-4
    4. Molecular Formula: C11H22O3
    5. Molecular Weight: 202.29058
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 114607-20-4.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 283.4°Cat760mmHg
    3. Flash Point: 108.6°C
    4. Appearance: /
    5. Density: 0.953g/cm3
    6. Vapor Pressure: 0.000368mmHg at 25°C
    7. Refractive Index: 1.442
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.45±0.20(Predicted)
    11. CAS DataBase Reference: sitophilate(CAS DataBase Reference)
    12. NIST Chemistry Reference: sitophilate(114607-20-4)
    13. EPA Substance Registry System: sitophilate(114607-20-4)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 114607-20-4(Hazardous Substances Data)

114607-20-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 114607-20-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,4,6,0 and 7 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 114607-20:
(8*1)+(7*1)+(6*4)+(5*6)+(4*0)+(3*7)+(2*2)+(1*0)=94
94 % 10 = 4
So 114607-20-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H22O3/c1-5-9(6-2)14-11(13)8(4)10(12)7-3/h8-10,12H,5-7H2,1-4H3/t8-,10+/m0/s1

114607-20-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name pentan-3-yl (2S,3R)-3-hydroxy-2-methylpentanoate

1.2 Other means of identification

Product number -
Other names Sitophilate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:114607-20-4 SDS

114607-20-4Relevant articles and documents

THE CHEMICAL IDENTIFICATION OF THE GRANARY WEEVIL AGGREGATION PHEROMONE

Phillips, Joel K.,Miller, Stephen P. F.,Andersen, John F.,Fales, Henry M.,Burkholder, Wendell E.

, p. 6145 - 6146 (1987)

(R*,S*)-1-Ethylpropyl 2-methyl-3-hydroxypentanoate is identified as the major component of the aggregation pheromone of Sitophilus granarius (L.), the granary weevil.

New synthesis of (±)-sitophilate using carboxylic acid dianion methodology - A stereoselectivity study

Gil, Salvador,Parra, Margarita,Rodriguez, Pablo,Sotoca, Enrique

, p. 3451 - 3455 (2007/10/03)

A simple two-step synthesis of (±)-sitophilate in has been developed by addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions. Efforts to control the diastereoselectiv-ity to generate the syn isomer are described. A modest degree of asymmetric induction is found using chiral amides as base. Georg Thieme Verlag Stuttgart.

Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis-Hillman adducts. Total synthesis of (±)-sitophilate

Mateus, Cristiano R,Feltrin, Melissa P,Costa, Ana M,Coelho, Fernando,Almeida, Wanda P

, p. 6901 - 6908 (2007/10/03)

We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes.

STEREOCHEMICALLY CONTROLLED SYNTHESIS OF RACEMIC SITOPHILATE, THE AGGREGATIONAL PHEROMONE OF THE GRAIN WEEVIL

Cheskis, B. A.,Moiseenkov, A. M.,Shpiro, N. A.,Stashina, G. A.,Zhulin, V. M.

, p. 716 - 720 (2007/10/02)

Controlled condensation of propionaldehyde with Li- or Si-enolates, generated from sec-amyl propionate, readily afforded a mixture of diastereomeric 2-methyl-3-hydroxypentanoic acid 3-pentyl esters, which were easily separated by chromatography.The erythr

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