(1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.02,7]dodecan]-5'-en-4'-one

• ChemBase ID: 132295
• Molecular Formular: C15H20O6
• Molecular Mass: 296.3157
• Monoisotopic Mass: 296.12598836
• SMILES: CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]1(C[C@H]([C@H]([C@]31CO3)O2)O)C)CO
• Canonical SMILES: OC[C@@]12[C@@H](C=C(C(=O)[C@H]1O)C)O[C@H]1[C@]3([C@]2(C)C[C@H]1O)CO3
• InChI: InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1
• InChIKey: LINOMUASTDIRTM-QGRHZQQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^2,^7]dodecan]-5'-en-4'-one
• IUPAC Traditional name: vomitoxin
• Synonyms: Deoxynivalenol; Deoxynivalenol solution; 3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one; Vomitoxin; DON; Deoxynivalenol solution; 4-Deoxynivalenol in acetonitrile; (3α,7α)-12,13-Epoxy-3,7,15-trihydroxytrichothec-9-en-8-one; 4-Deoxynivalenol; 4-Desoxynivalenol; Dehydronivalenol; NSC 269144; Deoxynivalenol; 3a,7a,15-三羟基-12,13-环氧单端孢霉-9-烯-8-酮; 呕吐毒素; 脱氧雪腐镰刀菌烯醇; 脱氧雪腐镰刀菌烯醇 溶液; 脱氧雪腐镰刀菌烯醇 溶液; 脱氧雪腐镰刀菌烯醇的乙腈溶液

Database IDs

• CAS Number: 51481-10-8
• EC Number: 200-835-2
• MDL Number: MFCD09039270
• PubChem SID: 24860915; 162226572; 24893213
• PubChem CID: 40024

CALCULATED PROPERTIES

• Acid pKa: 12.679138
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.9686969
• LogD (pH = 7.4): -0.96869916
• Log P: -0.9686969
• Molar Refractivity: 71.6206 cm^3
• Polarizability: 28.64595 Å^3
• Polar Surface Area: 99.52 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 2 °C; 26.6 °F; -3 °C; 35.6 °F

Safety Information

• RTECS: YD0167000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1648; 1993; 2811
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 11-20/21/22-36-66-68/20/21/22; 25
• Safety Statements: 16-26-36/37; 16-36/37; 36/37/39-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H225-H302-H319-H336-H371; H300
• GHS Precautionary statements: P210-P260-P305 + P351 + P338; P210-P280-P305 + P351 + P338; P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1648 3/PG 2; UN 1993 3/PG 2; UN 2811 6.1/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (TLC)
• Concentration: 100 μg/mL in acetonitrile; 200 μg/mL in ethyl acetate: methanol (95:5)
• Grade: analytical standard; analytical standard, for environmental analysis; BCR® certified Reference Material
• Packaging: ampule of 1 mL
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C15H20O6

DETAILS

Sigma Aldrich - 34124

General description
Certan Vial

Sigma Aldrich - IRMM315

Legal Information
BCR is a registered trademark of European Commission

Toronto Research Chemicals - D243900

Deoxynivalenol is a tricothecene mycotoxin and potent protein synthesis inhibitor. Deoxynivalenol exhibits cytotoxic activity in vivo via the ribotoxic stress response. Deoxynivalenol induces p38-mediated gene expression and apoptosis in leukocytes; activ

REFERENCES

• Bae, et al.: Toxicol. Sci., 105, 59 (2008)
• Shi, et al.: Toxicol. Sci., 109, 247 (2008)
• Krishnaswamy, et al.: Free Radic. Biol. Med., 49 50 (2008)