(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione

• ChemBase ID: 137876
• Molecular Formular: C16H23NO6
• Molecular Mass: 325.35692
• Monoisotopic Mass: 325.15253746
• SMILES: C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O
• Canonical SMILES: O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O
• InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
• InChIKey: QVCMHGGNRFRMAD-XFGHUUIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^1^3,^1^6]hexadec-10-ene-3,7-dione
• IUPAC Traditional name: monocrotaline
• Synonyms: Monocrotaline; Crotaline; Crotaline; Monocrotaline; 野百合碱; 单响尾蛇毒蛋白; 单响尾蛇毒蛋白; 野百合碱

Database IDs

• CAS Number: 315-22-0
• MDL Number: MFCD00084656
• Beilstein Number: 48732
• PubChem SID: 162232137
• PubChem CID: 9415

CALCULATED PROPERTIES

• Acid pKa: 11.494293
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.866132
• LogD (pH = 7.4): -1.0958016
• Log P: -0.33238804
• Molar Refractivity: 80.7028 cm^3
• Polarizability: 32.17088 Å^3
• Polar Surface Area: 96.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble50 mg/mL, clear, slightly yellow
• Melting Point: 204 °C (dec.)(lit.)
• Optical Rotation: [α]19/D -54.8°, c = 5 in chloroform

Safety Information

• RTECS: QB3140000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-40
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: 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 1544 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (TLC); 99%
• Grade: analytical standard
• Empirical Formula (Hill Notation): C16H23NO6

DETAILS

Sigma Aldrich - 27975

Other Notes
Provides a defense weapon for the eggs of the moth Utetheisa ornatrix1

Sigma Aldrich - 37024

Reconstitution
Dried down, 100 μg/mL after reconstitution with 1 mL of water