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W237809

Sigma-Aldrich

Diethyl L-tartrate

≥99%, FG

Synonym(s):

(+)-Diethyl L-tartrate, L-(+)-Tartaric acid diethyl ester

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About This Item

Linear Formula:
[-CH(OH)CO2C2H5]2
CAS Number:
87-91-2
Molecular Weight:
206.19
FEMA Number:
2378
Beilstein:
1727145
EC Number:
201-783-3
Council of Europe no.:
440
MDL number:
MFCD00009143
UNSPSC Code:
12164502
PubChem Substance ID:
24901033
Flavis number:
9.446
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117
FDA 21 CFR 172.515

Assay

≥99%

optical activity

[α]20/D +8.5°, neat

refractive index

n20/D 1.446 (lit.)

bp

280 °C (lit.)

density

1.204 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

fruity; wine-like

SMILES string

CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC

InChI

1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1

InChI key

YSAVZVORKRDODB-PHDIDXHHSA-N

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Application


  • Synthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions.: This study synthesizes l-threitol-based crown ethers using diethyl ʟ-tartrate and explores their efficacy as enantioselective phase transfer catalysts in Michael additions, highlighting their potential in asymmetric synthesis (Rapi et al., 2017).

  • A facile approach for the synthesis of C13-C24 fragments of maltepolides A, C and D.: This research demonstrates a novel synthesis method for C13-C24 fragments of maltepolides A, C, and D using diethyl ʟ-tartrate, facilitating the study and development of these bioactive compounds (Rao & Srihari, 2016).

  • Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C.: This research introduces diacyltetrol lipids synthesized from diethyl ʟ-tartrate, which act as activators for the C1 domain of protein kinase C, offering insights into signal transduction and therapeutic applications (Mamidi et al., 2012).

  • Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol.: The paper presents the total synthesis of broussonetine F, utilizing diethyl ʟ-tartrate in an orthoamide Overman rearrangement, showcasing a novel synthetic route for complex natural products (Hama et al., 2011).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

199.4 °F - closed cup

Flash Point(C)

93 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kimberly A Kahle et al.
Electrophoresis, 28(15), 2644-2657 (2007-06-29)
In this second study on dual-chirality microemulsions containing a chiral surfactant and a chiral oil, a less hydrophobic and lower interfacial tension chiral oil, diethyl tartrate, is employed (Part 1, Foley, J. P. et al.., Electrophoresis, DOI: 10.1002/elps.200600551). Six stereochemical
Aman Ullah et al.
Biomacromolecules, 12(10), 3826-3832 (2011-09-06)
Poultry feather quills have been extruded in a twin screw extruder with sodium sulfite treatment as a reducing agent. The effect of four different plasticizers (ethylene glycol, propylene glycol, glycerol, and diethyl tartrate) on the thermoplastic properties was then investigated.
Naoki Miyakoshi et al.
The Journal of organic chemistry, 70(15), 6045-6052 (2005-07-16)
A highly stereoselective method for constructing a (2E)-methoxymethylidene-1,6-dioxaspiro[4.5]decane skeleton has been developed on the basis of the palladium(II)-catalyzed ring-closing reaction of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivatives as a crucial step. The newly developed procedures could be successfully applied to the first total
Chi-Hung Wu et al.
Electrophoresis, 28(20), 3691-3696 (2007-09-26)
A novel microemulsion based on a mixture of diethyl L-tartrate (DET) and SDS was developed for the microemulsion EKC (MEEKC) determination of structurally related steroids. The system consisted of 0.5% w/w DET, 1.7% w/w SDS, 1.2% w/w 1-butanol, 89.6% w/w
Naoto Hama et al.
Organic letters, 13(4), 616-619 (2011-01-05)
A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.
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