DOTMA E-isomer

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MedKoo CAT#: 556228

CAS#: 104872-42-6 (E-isomer chloride)

Description: DOTMA E-isomer is a trans-isomer of DOTMA, in which two double bonds are trans-configuration (configuration of a geometrical isomer in which two groups are on opposite sides of an imaginary reference line on the molecule). DOTMA E-isomer is a useful cationic lipid for gene transfection, nucleic acids delivery, plasmid stabilization. Note: DOTMA is the Z-isomer (or Cis-isomer) chloride salt, which CAS# is 104162-48-3. While DOTMA E-isomer (trans-isomer) chloride salt has CAS#104872-42-6. Some vendors confused each other.

Chemical Structure

DOTMA E-isomer
CAS# 104872-42-6 (E-isomer chloride)

Theoretical Analysis

MedKoo Cat#: 556228
Name: DOTMA E-isomer
CAS#: 104872-42-6 (E-isomer chloride)
Chemical Formula: C42H84ClNO2
Exact Mass:
Molecular Weight: 670.589
Elemental Analysis: C, 75.23; H, 12.63; Cl, 5.29; N, 2.09; O, 4.77

Price and Availability

Size Price Availability Quantity
25.0mg USD 110.0 Ready to Ship
50.0mg USD 190.0 Ready to Ship
100.0mg USD 350.0 Ready to Ship
200.0mg USD 550.0 Ready to Ship
500.0mg USD 1250.0 Ready to Ship
1.0g USD 2050.0 Ready to Ship
2.0g USD 3850.0 Ready to Ship
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Related CAS #: 104162-48-3 (Z-isomer chloride)   122342-03-4 (Z-isomer cation)   104872-42-6 (E-isomer chloride)   717090-94-3 (E-isomer cation)    

Synonym: DOTMA E-isomer chlrodie;

IUPAC/Chemical Name: 1-Propanaminium, N,N,N-trimethyl-2,3-bis(9-octadecen-1-yloxy)-, chloride (1:1)


InChi Code: InChI=1S/C42H84NO2.ClH/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-44-41-42(40-43(3,4)5)45-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2;/h20-23,42H,6-19,24-41H2,1-5H3;1H/q+1;/p-1/b22-20+,23-21+;


Appearance: To be determined

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Preparing Stock Solutions

The following data is based on the product molecular weight 670.589 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

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1: Gendron F, Grasser M, Le Guennic B. Near-infrared circular dichroism of the ytterbium DOTMA complex: an ab initio investigation. Phys Chem Chem Phys. 2022 Mar 2;24(9):5404-5410. doi: 10.1039/d1cp01675j. PMID: 35170600.

2: Woods M, Payne KM, Valente EJ, Kucera BE, Young VG Jr. Crystal Structures of DOTMA Chelates from Ce3+ to Yb3+ : Evidence for a Continuum of Metal Ion Hydration States. Chemistry. 2019 Jul 25;25(42):9997-10005. doi: 10.1002/chem.201902068. Epub 2019 Jul 3. PMID: 31121070; PMCID: PMC6700027.

3: Mashal M, Attia N, Puras G, Martínez-Navarrete G, Fernández E, Pedraz JL. Retinal gene delivery enhancement by lycopene incorporation into cationic niosomes based on DOTMA and polysorbate 60. J Control Release. 2017 May 28;254:55-64. doi: 10.1016/j.jconrel.2017.03.386. Epub 2017 Mar 24. PMID: 28347807.

4: Kumas C, Fernando WS, Zhao P, Regueiro-Figueroa M, Kiefer GE, Martins AF, Platas-Iglesias C, Sherry AD. Unexpected Changes in the Population of Coordination Isomers for the Lanthanide Ion Complexes of DOTMA-Tetraglycinate. Inorg Chem. 2016 Sep 19;55(18):9297-305. doi: 10.1021/acs.inorgchem.6b01390. Epub 2016 Sep 7. PMID: 27603690; PMCID: PMC5221692.

5: Webber BC, Woods M. Structural analysis of isomeric europium(III) chelates of NB-DOTMA. Inorg Chem. 2012 Aug 6;51(15):8576-82. doi: 10.1021/ic3011597. Epub 2012 Jul 18. PMID: 22809081.

6: Aime S, Botta M, Garda Z, Kucera BE, Tircso G, Young VG, Woods M. Properties, solution state behavior, and crystal structures of chelates of DOTMA. Inorg Chem. 2011 Sep 5;50(17):7955-65. doi: 10.1021/ic2012827. Epub 2011 Aug 5. PMID: 21819052; PMCID: PMC3204394.

7: Matsumoto M, Kishikawa R, Kurosaki T, Nakagawa H, Ichikawa N, Hamamoto T, To H, Kitahara T, Sasaki H. Hybrid vector including polyethylenimine and cationic lipid, DOTMA, for gene delivery. Int J Pharm. 2008 Nov 3;363(1-2):58-65. doi: 10.1016/j.ijpharm.2008.07.010. Epub 2008 Jul 18. PMID: 18687391.

8: Gaucheron J, Santaella C, Vierling P. Transfection with fluorinated lipoplexes based on fluorinated analogues of DOTMA, DMRIE and DPPES. Biochim Biophys Acta. 2002 Aug 31;1564(2):349-58. doi: 10.1016/s0005-2736(02)00469-8. PMID: 12175917.

9: Ren T, Song YK, Zhang G, Liu D. Structural basis of DOTMA for its high intravenous transfection activity in mouse. Gene Ther. 2000 May;7(9):764-8. doi: 10.1038/ PMID: 10822303.

10: Wollenberg B, Kastenbauer, Mundl H, Schaumberg J, Mayer A, Andratschke M, Lang S, Pauli C, Zeidler R, Ihrler S, Löhrs, Naujoks K, Rollston R. Gene therapy --phase I trial for primary untreated head and neck squamous cell cancer (HNSCC) UICC stage II-IV with a single intratumoral injection of hIL-2 plasmids formulated in DOTMA/Chol. Hum Gene Ther. 1999 Jan 1;10(1):141-7. doi: 10.1089/10430349950019273. PMID: 10022539.

11: Konopka K, Davis BR, Düzgüneş N. HIV-1 infection of a non-CD4-expressing variant of HUT-78 cells: lack of inhibition by Leu3A antibodies and enhancement by cationic DOTMA liposomes. Adv Exp Med Biol. 1991;300:97-110. doi: 10.1007/978-1-4684-5976-0_7. PMID: 1781348.