MedKoo Cat#: 597037 | Name: Diisopropyl tartrate
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diisopropyl tartrate is a reagent for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation.

Chemical Structure

Diisopropyl tartrate
CAS#2217-15-4

Theoretical Analysis

MedKoo Cat#: 597037

Name: Diisopropyl tartrate

CAS#: 2217-15-4

Chemical Formula: C10H18O6

Exact Mass: 234.1103

Molecular Weight: 234.25

Elemental Analysis: C, 51.27; H, 7.75; O, 40.98

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
(+)-Diisopropyl L-tartrate; (2R,3R)-Diisopropyl 2,3-dihydroxysuccinate; Diisopropyl L-(+)-Tartrate; (+)-DIPT
IUPAC/Chemical Name
dipropan-2-yl (2R,3R)-2,3-dihydroxybutanedioate
InChi Key
XEBCWEDRGPSHQH-HTQZYQBOSA-N
InChi Code
InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m1/s1
SMILES Code
O=C(OC(C)C)[C@H](O)[C@@H](O)C(OC(C)C)=O
Appearance
Liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Diisopropyl tartrate is a reagent for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation.
In vitro activity:
The current work reports an extended theoretical study from our previous experimental work for the enantioselective extraction of amlodipine enantiomers in a biphasic recognition chiral extraction system (BRCES) consisting of hydrophobic D-diisopropyl tartrate dissolved in organic phase (n-decanol) and hydrophilic hydroxypropyl-β-cyclodextrin (HP-β-CD) in aqueous phase (acetate buffer) which preferentially recognize the R-enantiomer and S-enantiomer, respectively. Reference: Sci Pharm. 2015 Jun 22;83(4):683-98. https://pubmed.ncbi.nlm.nih.gov/26839848/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 234.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Al Azzam KM, Abdallah HH, Halim HN, Ahmad MA, Shaibah H. Host-Guest Inclusion Complexes between Amlodipine Enantiomers in the Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation by using their Enantioselective Extraction. Sci Pharm. 2015 Jun 22;83(4):683-98. doi: 10.3797/scipharm.1501-15. PMID: 26839848; PMCID: PMC4727725. 2. Isoda M, Sato K, Tokura Y, Tarui A, Omote M, Ando A. Asymmetric reductive aldol-type reaction with carbonyl compounds using dialkyl tartrate as a chiral ligand. Chem Pharm Bull (Tokyo). 2014;62(10):956-61. doi: 10.1248/cpb.c14-00223. PMID: 25273054.
In vitro protocol:
1. Al Azzam KM, Abdallah HH, Halim HN, Ahmad MA, Shaibah H. Host-Guest Inclusion Complexes between Amlodipine Enantiomers in the Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation by using their Enantioselective Extraction. Sci Pharm. 2015 Jun 22;83(4):683-98. doi: 10.3797/scipharm.1501-15. PMID: 26839848; PMCID: PMC4727725. 2. Isoda M, Sato K, Tokura Y, Tarui A, Omote M, Ando A. Asymmetric reductive aldol-type reaction with carbonyl compounds using dialkyl tartrate as a chiral ligand. Chem Pharm Bull (Tokyo). 2014;62(10):956-61. doi: 10.1248/cpb.c14-00223. PMID: 25273054.
In vivo protocol:
TBD
1: Al Azzam KM, Abdallah HH, Halim HN, Ahmad MA, Shaibah H. Host-Guest Inclusion Complexes between Amlodipine Enantiomers in the Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation by using their Enantioselective Extraction. Sci Pharm. 2015 Jun 22;83(4):683-98. doi: 10.3797/scipharm.1501-15. Print 2015 Oct-Dec. PubMed PMID: 26839848; PubMed Central PMCID: PMC4727725. 2: Prakash L, Himaja M, Vasudev R. Isolation, Identification, and Characterisation of Degradation Products and the Development and Validation of a Stability-Indicating Method for the Estimation of Impurities in the Tolterodine Tartrate Formulation. Sci Pharm. 2014 Sep 8;83(1):65-83. doi: 10.3797/scipharm.1407-18. Print 2015 Jan-Mar. PubMed PMID: 26839802; PubMed Central PMCID: PMC4727816. 3: Isoda M, Sato K, Tokura Y, Tarui A, Omote M, Ando A. Asymmetric reductive aldol-type reaction with carbonyl compounds using dialkyl tartrate as a chiral ligand. Chem Pharm Bull (Tokyo). 2014;62(10):956-61. PubMed PMID: 25273054. 4: Yoshida M, Sassa N, Kato T, Fujinami S, Soeta T, Inomata K, Ukaji Y. Desymmetrization of 1,4-pentadien-3-ol by the asymmetric 1,3-dipolar cycloaddition of azomethine imines. Chemistry. 2014 Feb 10;20(7):2058-64. doi: 10.1002/chem.201302889. Epub 2014 Jan 8. PubMed PMID: 24403279. 5: Prakash L, Himaja M, Subbaiah BV, Vasudev R, Srinivasulu C, Haribabu R. Isolation, identification and characterization of degradant impurities in Tolterodine tartrate formulation. J Pharm Biomed Anal. 2014 Mar;90:215-21. doi: 10.1016/j.jpba.2013.12.007. Epub 2013 Dec 15. PubMed PMID: 24384498. 6: Laurenson JA, Parkinson JA, Percy JM, Rinaudo G, Roig R. Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate. Beilstein J Org Chem. 2013 Nov 26;9:2660-8. doi: 10.3762/bjoc.9.301. eCollection 2013. PubMed PMID: 24367430; PubMed Central PMCID: PMC3869297. 7: Antunes Nde J, Cavalli RC, Marques MP, Lanchote VL. Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy. Chirality. 2013 Jan;25(1):1-7. doi: 10.1002/chir.22102. Epub 2012 Oct 24. PubMed PMID: 23097090. 8: Sun H, Roush WR, Candito DA, Blanchot M, Lautens M. SYNTHESIS OF (S,S)-DIISOPROPYL TARTRATE (E)-CROTYLBORONATE AND ITS REACTION WITH ALDEHYDES: (2R,3R,4R)-1,2-DIDEOXY-2-ETHENYL-4,5-O-(1-METHYLETHYLIDENE)-XYLITOL. Organic Synth. 2011;88:181-196. PubMed PMID: 21666877; PubMed Central PMCID: PMC3111236. 9: Zhang P, Polavarapu PL. Spectroscopic investigation of the structures of dialkyl tartrates and their cyclodextrin complexes. J Phys Chem A. 2007 Feb 8;111(5):858-71. PubMed PMID: 17266226. 10: Chen WS, Chen ZR. Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate. J Zhejiang Univ Sci B. 2005 Jun;6(6):606-10. PubMed PMID: 15909353; PubMed Central PMCID: PMC1389899. 11: Kosutić-Hulita N, Zegarac M. Tolterodinium (+)-(2R,3R)-hydrogen tartrate. Acta Crystallogr C. 2005 Mar;61(Pt 3):o171-3. Epub 2005 Feb 19. PubMed PMID: 15750247. 12: Rahimy M, Hallén B, Narang P. Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers. Arzneimittelforschung. 2002;52(12):890-5. PubMed PMID: 12572529. 13: Okachi T, Murai N, Onaka M. Catalytic enantioselective epoxidation of homoallylic alcohols by chiral zirconium complexes. Org Lett. 2003 Jan 9;5(1):85-7. PubMed PMID: 12509897. 14: Mukai C, Moharram SM, Azukizawa S, Hanaoka M. Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2. J Org Chem. 1997 Nov 14;62(23):8095-8103. PubMed PMID: 11671917. 15: Påhlman I, Kankaanranta S, Palmér L. Pharmacokinetics of tolterodine, a muscarinic receptor antagonist, in mouse, rat and dog. Interspecies relationship comparing with human pharmacokinetics. Arzneimittelforschung. 2001 Feb;51(2):134-44. Erratum in: Arzneimittelforschung 2001;51(4):339. PubMed PMID: 11258043. 16: Påhlman I, d'Argy R, Nilvebrant L. Tissue distribution of tolterodine, a muscarinic receptor antagonist, and transfer into fetus and milk in mice. Arzneimittelforschung. 2001 Feb;51(2):125-33. PubMed PMID: 11258042. 17: Micalizio GC, Roush WR. A three-component coupling strategy for tetrahydrofuran synthesis: application of the diisopropyl tartrate modified (E)-gamma-(dimethylphenylsilyl)allylboronate as an alpha,gamma-allyl dianion equivalent. Org Lett. 2000 Feb 24;2(4):461-4. PubMed PMID: 10814351. 18: Yono M, Yoshida M, Wada Y, Kikukawa H, Takahashi W, Inadome A, Seshita H, Ueda S. Pharmacological effects of tolterodine on human isolated urinary bladder. Eur J Pharmacol. 1999 Mar 5;368(2-3):223-30. PubMed PMID: 10193658. 19: Gillberg PG, Sundquist S, Nilvebrant L. Comparison of the in vitro and in vivo profiles of tolterodine with those of subtype-selective muscarinic receptor antagonists. Eur J Pharmacol. 1998 May 22;349(2-3):285-92. PubMed PMID: 9671109. 20: Nilvebrant L, Gillberg PG, Sparf B. Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine. Pharmacol Toxicol. 1997 Oct;81(4):169-72. PubMed PMID: 9353847.