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MedKoo Cat#: 573634 | Name: Meldrum's acid
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Description:

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

Meldrum's acid is an antimicrobial agent of deodorant composition.

Chemical Structure

Meldrum's acid
Meldrum's acid
CAS#2033-24-1

Theoretical Analysis

MedKoo Cat#: 573634

Name: Meldrum's acid

CAS#: 2033-24-1

Chemical Formula: C6H8O4

Exact Mass: 144.0423

Molecular Weight: 144.13

Elemental Analysis: C, 50.00; H, 5.60; O, 44.40

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 weeks
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Related CAS #
No Data
Synonym
AI3-39039, Isopropylidene malonate, Meldrum's acid
IUPAC/Chemical Name
1,3-Dioxane-4,6-dione, 2,2-dimethyl-
InChi Key
GXHFUVWIGNLZSC-UHFFFAOYSA-N
InChi Code
1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
SMILES Code
C1(OC(CC(O1)=O)=O)(C)C
Appearance
Solid powder
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
>3 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
Product Data
Instruction
View handling instruction
Biological target:
Meldrum's acid is an antimicrobial agent of deodorant composition.
In vitro activity:
The first total syntheses of (±)-catellatolactams A and B, two novel ansamacrolactams, are described in 5 and 8 steps, respectively. The strategy relies on an amidation reaction to couple the acylated Meldrum's acid and an aryl amine, a regioselective C-H insertion to construct the γ-lactam moiety, and an RCM reaction to forge the macrocycles with E-olefin. This concise and scalable synthesis provided over 200 mg of the target molecules. Reference: Org Lett. 2023 Feb 17;25(6):1003-1007. https://pubmed.ncbi.nlm.nih.gov/36748956/
In vivo activity:
1,3-Substituted pyrazolo[3,4-b]pyridinones 11-18 were synthesized by a three-component condensation of Meldrum's acid with aryl aldehydes and 1,3-substituted 5-aminopyrazoles. In the sea urchin embryo model, 1-benzimidazolyl-pyrazolo[3,4-b]pyridinones 11 caused inhibition of hatching and spiculogenesis at sub-micromolar concentrations. Reference: ACS Comb Sci. 2019 Dec 9;21(12):805-816. https://pubmed.ncbi.nlm.nih.gov/31689077/

Preparing Stock Solutions

The following data is based on the product molecular weight 144.13 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. Yang H, Zhang Y, Chen W, Shi H, Huo L, Li J, Li H, Xie X, She X. Scalable Total Syntheses of (±)-Catellatolactams A and B. Org Lett. 2023 Feb 17;25(6):1003-1007. doi: 10.1021/acs.orglett.3c00132. Epub 2023 Feb 7. PMID: 36748956. 2. Dotsenko VV, Aksenov AV, Sinotsko AE, Varzieva EA, Russkikh AA, Levchenko AG, Aksenov NA, Aksenova IV. The Reactions of N,N'-Diphenyldithiomalondiamide with Arylmethylidene Meldrum's Acids. Int J Mol Sci. 2022 Dec 15;23(24):15997. doi: 10.3390/ijms232415997. PMID: 36555639; PMCID: PMC9785638. 3. Lichitsky BV, Komogortsev AN, Dudinov AA, Krayushkin MM, Khodot EN, Samet AV, Silyanova EA, Konyushkin LD, Karpov AS, Gorses D, Radimerski T, Semenova MN, Kiselyov AS, Semenov VV. Benzimidazolyl-pyrazolo[3,4-b]pyridinones, Selective Inhibitors of MOLT-4 Leukemia Cell Growth and Sea Urchin Embryo Spiculogenesis: Target Quest. ACS Comb Sci. 2019 Dec 9;21(12):805-816. doi: 10.1021/acscombsci.9b00135. Epub 2019 Nov 14. PMID: 31689077. 4. Hussein B, Ikhmais B, Kadirvel M, Magwaza RN, Halbert G, Bryce RA, Stratford IJ, Freeman S. Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinoneoxidoreductase-2 (NQO2). Eur J Med Chem. 2019 Nov 15;182:111649. doi: 10.1016/j.ejmech.2019.111649. Epub 2019 Aug 27. PMID: 31514018.
In vitro protocol:
1. Yang H, Zhang Y, Chen W, Shi H, Huo L, Li J, Li H, Xie X, She X. Scalable Total Syntheses of (±)-Catellatolactams A and B. Org Lett. 2023 Feb 17;25(6):1003-1007. doi: 10.1021/acs.orglett.3c00132. Epub 2023 Feb 7. PMID: 36748956. 2. Dotsenko VV, Aksenov AV, Sinotsko AE, Varzieva EA, Russkikh AA, Levchenko AG, Aksenov NA, Aksenova IV. The Reactions of N,N'-Diphenyldithiomalondiamide with Arylmethylidene Meldrum's Acids. Int J Mol Sci. 2022 Dec 15;23(24):15997. doi: 10.3390/ijms232415997. PMID: 36555639; PMCID: PMC9785638.
In vivo protocol:
1. Lichitsky BV, Komogortsev AN, Dudinov AA, Krayushkin MM, Khodot EN, Samet AV, Silyanova EA, Konyushkin LD, Karpov AS, Gorses D, Radimerski T, Semenova MN, Kiselyov AS, Semenov VV. Benzimidazolyl-pyrazolo[3,4-b]pyridinones, Selective Inhibitors of MOLT-4 Leukemia Cell Growth and Sea Urchin Embryo Spiculogenesis: Target Quest. ACS Comb Sci. 2019 Dec 9;21(12):805-816. doi: 10.1021/acscombsci.9b00135. Epub 2019 Nov 14. PMID: 31689077. 2. Hussein B, Ikhmais B, Kadirvel M, Magwaza RN, Halbert G, Bryce RA, Stratford IJ, Freeman S. Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinoneoxidoreductase-2 (NQO2). Eur J Med Chem. 2019 Nov 15;182:111649. doi: 10.1016/j.ejmech.2019.111649. Epub 2019 Aug 27. PMID: 31514018.
1: Trujillo C, Goya P, Rozas I. Study of Meldrum's Acid Cyclization Reactions. J Phys Chem A. 2018 Mar 8;122(9):2535-2541. doi: 10.1021/acs.jpca.7b11818. Epub 2018 Feb 27. PubMed PMID: 29465244. 2: Wu J, Iacono ST, McCandless GT, Smith DW Jr, Novak BM. Utilization of a Meldrum's acid towards functionalized fluoropolymers possessing dual reactivity for thermal crosslinking and post-polymerization modification. Chem Commun (Camb). 2015 Jun 4;51(44):9220-2. doi: 10.1039/c5cc02382c. PubMed PMID: 25952621.

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