Synonym
Lithium Carmine; Natural Red 2180; Natural Red 4; NSC 326224;
IUPAC/Chemical Name
lithium 3,5,5,6-tetrahydroxy-1-methyl-9,10-dioxo-7-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-9,10-dihydro-5l5-anthracene-2-carboxylate
InChi Key
LJNAVNXQDNJKIJ-FJASXRKZSA-M
InChi Code
InChI=1S/C22H20O13.Li/c1-4-8-5(2-6(24)9(4)22(33)34)13(25)10-11(15(8)27)16(28)12(18(30)17(10)29)21-20(32)19(31)14(26)7(3-23)35-21;/h2,7,14,19-21,23-24,26,28-32H,3H2,1H3,(H,33,34);/q;-1/p-1/t7-,14-,19+,20-,21+;/m1./s1
SMILES Code
O=C1C2=C(O)C([C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)=C(O)C(O)=C2C(C4=CC(O)=C(C([O-])=O)C(C)=C41)=O.[Li-]
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
498.32
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.
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 |
1: Kawai Y, Smedsrød B, Elvevold K, Wake K. Uptake of lithium carmine by sinusoidal endothelial and Kupffer cells of the rat liver: new insights into the classical vital staining and the reticulo-endothelial system. Cell Tissue Res. 1998 May;292(2):395-410. PubMed PMID: 9560481.
2: SCHMIDT-RAMSIN D. [Studies on a new method of blood sedimentation with lithium carmine]. Z Gesamte Inn Med. 1953 Jul 1;8(13):581-91. Undetermined Language. PubMed PMID: 13170088.
3: Rolle DJ, Kretschmar KH. [On the angio-architecture of intramuscularly implanted Yoshida-sarcoma in untreated and lithium carmine-treated rats (author's transl)]. Zentralbl Allg Pathol. 1976;120(5):383-90. German. PubMed PMID: 1014966.
4: TETI M, MESSORE G. [Effect of testicular mesomucinase on capillary permeability. III. The reticuloendothelial system of rabbits treated over a period of four weeks with intravenous lithium carmine and hyaluronidase]. Riv Ist Sieroter Ital. 1952 Sep-Oct;27(5):380-5. Undetermined Language. PubMed PMID: 13028067.
5: Yao M, Kuratani K, Kojima T, Takeichi N, Senoh H, Kiyobayashi T. Indigo carmine: an organic crystal as a positive-electrode material for rechargeable sodium batteries. Sci Rep. 2014 Jan 13;4:3650. doi: 10.1038/srep03650. PubMed PMID: 24413423; PubMed Central PMCID: PMC3888987.
6: Dapson RW, Frank M, Penney DP, Kiernan JA. Revised procedures for the certification of carmine (C.I. 75470, Natural red 4) as a biological stain. Biotech Histochem. 2007 Feb;82(1):13-5. PubMed PMID: 17510809.
7: Schlüter G. [Effects of lithium carmine and lithium carbonate on the prenatal development of mice]. Naunyn Schmiedebergs Arch Pharmakol. 1971;270(1):56-64. German. PubMed PMID: 4253064.
8: Gestewitz HR, Wulf E. [Binding of the reticuloendotheliotropic vital dye-stuffs lithium carmine and trypan blue to plasma proteins]. Acta Histochem. 1973;46(1):18-37. German. PubMed PMID: 4210093.
9: Picard JJ, Heremans JF. The binding of lithium carmine to alpha2-macroglobulin. Z Naturforsch B. 1969 Nov;24(11):1442-7. PubMed PMID: 4188599.
10: Schlüter G. Time-response-relationship of embryotoxic effects of lithium carmine in mice. Naunyn Schmiedebergs Arch Pharmakol. 1971;270(3):316-8. PubMed PMID: 4254629.
11: Wulf E. [Information on the reticuloendotheliotropic vital dyes lithium carmine and trypan blue]. Acta Histochem. 1973;46(1):38-52. German. PubMed PMID: 4209799.
12: Hirai K, Yoshimura H, Fujimoto M. [Site of potential difference measurements in renal tubules of newt by the lithium carmine method]. Nihon Seirigaku Zasshi. 1968;30(1):22-9. Japanese. PubMed PMID: 5692598.
13: Schlúter G. [The significance of the yolk sac placenta for the development of malformations due to trypan blue and lithium carmine]. Verh Anat Ges. 1971;66:575-8. German. PubMed PMID: 5161899.
14: Wake K, Kawai Y, Smedsrød B. Re-evaluation of the reticulo-endothelial system. Ital J Anat Embryol. 2001;106(2 Suppl 1):261-9. PubMed PMID: 11729964.
15: Schlüter G. [Embryotoxic action of carmine in mice]. Z Anat Entwicklungsgesch. 1970;131(3):228-35. German. PubMed PMID: 5528314.
16: Titford M. Comparison of historic Grübler dyes with modern counterparts. Biotech Histochem. 2001 Jan;76(1):23-30. PubMed PMID: 11440299.
17: Wake K. [One hundred years of sinusoidal cells in the liver]. Kaibogaku Zasshi. 1997 Oct;72(5):407-23. Review. Japanese. PubMed PMID: 9396207.
18: Takada N, Wada I, Sugimura I, Sakuma E, Maruyama H, Matsui N. A possible barrier function of the articular surface. Kaibogaku Zasshi. 1999 Dec;74(6):631-7. PubMed PMID: 10659579.
19: GRECZ N, DACK GM. Taxonomically significant color reactions of Brevibacterium linens. J Bacteriol. 1961 Aug;82:241-6. PubMed PMID: 13708147; PubMed Central PMCID: PMC279149.
20: Takahashi K, Sakuma H, Naito M, Yaginuma Y, Takahashi H, Asano S, Hojo H, Kojima M. Cytological characters, transformation, and ontogenesis of dermal histiocytes and fibroblasts of rats. Acta Pathol Jpn. 1980 Sep;30(5):743-66. PubMed PMID: 7446111.