6-bromocyclohex-4-ene-1,2,3-triol

• ChemBase ID: 91247
• Molecular Formular: C6H9BrO3
• Molecular Mass: 209.03786
• Monoisotopic Mass: 207.97350615
• SMILES: OC1C(C(C(C=C1)Br)O)O
• Canonical SMILES: OC1C=CC(C(C1O)O)Br
• InChI: InChI=1S/C6H9BrO3/c7-3-1-2-4(8)6(10)5(3)9/h1-6,8-10H
• InChIKey: SUCAFEYLYXXTPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-bromocyclohex-4-ene-1,2,3-triol
• IUPAC Traditional name: 6-bromocyclohex-4-ene-1,2,3-triol
• Synonyms: Bromoconduritol; 6-Bromo-3,4,5-trihydroxycyclohex-1-ene; 6-Bromocyclohex-4-ene-1,2,3-triol; 6-Bromo-3,4,5-trihydroxy Cyclohex-1-ene; 6-Bromo-4-cyclohexene-1,2,3-triol; Bromoconduritol (Mixture of Isomers); 6-BROMO-4-CYCLOHEXENE-1,2,3-TRIOL

Database IDs

• CAS Number: 42014-74-4
• MDL Number: MFCD00036927
• PubChem SID: 162077951
• PubChem CID: 122062

CALCULATED PROPERTIES

• Acid pKa: 12.759587
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.454037
• LogD (pH = 7.4): -0.45403886
• Log P: -0.45403698
• Molar Refractivity: 40.2031 cm^3
• Polarizability: 15.676994 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 115-118°C

Safety Information

• Storage Warning: Irritant/Store at -20°C

Product Information

• Purity: 99%

DETAILS

MP Biomedicals - 02158879

(6-Bromo-3,4,5-trihydroxycyclohex-1-ene; Bromoconduritol)
Purity: 99%
Mixed isomers
Inhibitor of mammalian α-glucosidase II over α-glucosidase I.

Apollo Scientific Ltd - OR6825T

Mixture of Isomers. Bromoconduritol inhibits mammalian aglucosidasde 2.

Toronto Research Chemicals - B682500

Bromoconduritol selectively inhibits mammalian alpha-glucosidase 2 (Glc2/Glc1 glucosidase in the glycoprotein processing pathway), yeast alpha-glucosidase, and some beta-glucosidases. It does not inhibit mammalian alpha-glucosidase 1 (Glc3-glucosidase)

REFERENCES

• Datema, R., et al., Proc. Natl. Acad. Sci. USA, 79: 678
• Proc. Natl. Acad. Sci. USA, 79, 6787-6791 (1982)
• Biochimie, 64, 977-1000 (1982)
• Trends Bio. Sci., 9, 32-34 (1984)