Cacotheline

• CAT Number: I023945
• CAS Number: 561-20-6
• Molecular Formula: C21H21N3O7
• Molecular Weight: 427.41
• Purity: 98%
• Synonyms: Cacotheline; NSC5069; NSC-5069; NSC 5069
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2-((4bS,7aS,8aR,13S,13aR,13bS)-1-nitro-2,3-dioxo-2,3,5,6,7a,8,8a,11,13,13a,13b,14-dodecahydro-7,9-methanooxepino[3,4-a]pyrrolo[2,3-d]carbazol-13-yl)acetic acid
• InChI: InChI=1S/C21H21N3O7/c25-12-6-11-17(18(19(12)28)24(29)30)22-20-16-10-5-14-21(11,20)2-3-23(14)8-9(10)1-4-31-13(16)7-15(26)27/h1,6,10,13-14,16,20,22H,2-5,7-8H2,(H,26,27)/t10-,13-,14-,16-,20-,21+/m0/s1
• InChIKey: IVEMPCACOMNRGI-OFDJEBHLSA-N
• SMILES: OC(C[C@@H]1OCC=C2CN3CC[C@@]45[C@@H]3C[C@@H]2[C@@H]1[C@@H]4NC6=C([N+]([O-])=O)C(C(C=C56)=O)=O)=O

Cacotheline is an organic compound with the chemical formula C₂₁H₂₁N₃O₇. It is a nitro derivative of brucine obtained by reaction of brucine with nitric acid. It is used as an indicator in the titrimetric analysis of tin ions.

Reference

1: Li M, Hu N, Lin S. Indirect measurement of brucine by adsorptive stripping voltammetry at mercury electrode. Talanta. 1995 Oct;42(10):1389-94. doi: 10.1016/0039-9140(95)01563-q. PMID: 18966368.
2: Murty NK, Rao VJ, Rao NV. Detection and determination of phenylhydrazine. Talanta. 1984 Jun;31(6):466. doi: 10.1016/0039-9140(84)80120-4. PMID: 18963630.
3: Murty NK, Dakshina Murty PM. Quantitative study of the reaction between quinones and iron(II) in phosphoric acid medium. Talanta. 1982 Mar;29(3):234-6. doi: 10.1016/0039-9140(82)80101-x. PMID: 18963119.
4: Murty NK, Satyanarayana V, Rao YF. Reductimetric determination of peroxydisulphate, hydrogen peroxide, sodium perborate, nitrate and nitrite in concentrated phosphoric acid medium with iron(II). Talanta. 1977 Dec;24(12):757-9. doi: 10.1016/0039-9140(77)80209-9. PMID: 18962193.
5: Chawla KL, Tandon JP. Vanadium compounds in reductimetric titrations-II Standardisation of vanadium(II) sulphate with common oxidising agents and determination of binary mixtures. Talanta. 1966 Apr;13(4):545-50. doi: 10.1016/0039-9140(66)80263-1. PMID: 18959914.
6: MEDVEDEVA IV. Kakotelinovyi metod opredeleniia oloba v pishchevykh produktakh [Cacotheline method of determination of tin in food products]. Vopr Pitan. 1958 Sep-Oct;17(5):69-73. Russian. PMID: 13604093.