(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one

• ChemBase ID: 103084
• Molecular Formular: C23H26N2O4
• Molecular Mass: 394.46354
• Monoisotopic Mass: 394.18925732
• SMILES: O=C1N2c3cc(OC)c(OC)cc3[C@@]34[C@@H]2[C@@H]2[C@@H](OCC=C5[C@@H]2C[C@@H]3N(CC4)C5)C1
• Canonical SMILES: COc1cc2c(cc1OC)N1[C@@H]3[C@@]42CCN2[C@H]4C[C@@H]4[C@H]3[C@H](CC1=O)OCC=C4C2
• InChI: InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
• InChIKey: RRKTZKIUPZVBMF-IBTVXLQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one; (1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^1,^1^8.0^2,^7.0^8,^2^2.0^1^1,^2^1.0^1^5,^2^0]tetracosa-2(7),3,5,14-tetraen-9-one; (1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^1,^1^8.0^2,^7.0^8,^2^2.0^1^1,^2^1.0^1^5,^2^0]tetracosa-2,4,6,14-tetraen-9-one
• IUPAC Traditional name: brucine
• Synonyms: Brucine, Anhydrous; 10,11-Dimethoxystrychnine; BRUCINE; Brucine; 2,3-Dimethoxystrychnine; 10,11-二甲氧基马钱子碱; 马钱子碱

Database IDs

• CAS Number: 357-57-3
• EC Number: 206-614-7
• MDL Number: MFCD00005942
• Beilstein Number: 63046
• PubChem SID: 24864782; 162091246
• PubChem CID: 442021
• CHEMBL: 501756
• Chemspider ID: 390579
• IUPHAR ligand ID: 342
• KEGG ID: C09084
• Unique Ingredient Identifier: 6NG17YCK6H
• Wikipedia Title: Brucine

CALCULATED PROPERTIES

• Acid pKa: 17.238964
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -2.5058765
• LogD (pH = 7.4): -0.84809655
• Log P: 0.6111788
• Molar Refractivity: 107.4341 cm^3
• Polarizability: 41.799164 Å^3
• Polar Surface Area: 51.24 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: >177°C (dec.); 175-177 °C; 175-178 °C (dec.)(lit.); 176-179 °C; 178°C
• Optical Rotation: [α]20/D -118°, c = 2.5 in chloroform; [α]20/D -119±2°, c = 2.5% in chloroform; [α]20/D -120±10°, c = 2.5% in chloroform

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere; Room Temperature (15-30°C)
• RTECS: EH8925000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1570
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Australian Hazchem: 2X
• Risk Statements: 26/28-52/53; R:26/28-52/53
• Safety Statements: 13-45-61; S:13-45-61
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 152
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H330-H412
• GHS Precautionary statements: P260-P264-P273-P284-P301 + P310-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1570 6.1/PG 1

Product Information

• Purity: ≥97.0% (TLC); ≥99.0% (TLC); 98%
• Grade: anhydrous; purum; purum p.a.
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ~3% water; ≤0.5% water
• Empirical Formula (Hill Notation): C23H26N2O4

DETAILS

MP Biomedicals - 02150526

Resolving agent

Sigma Aldrich - 399027

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 00614

Application
microreagent for the determination of nitrate

Sigma Aldrich - 18800

Application
Resolving agent for carboxylic acids