1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 5353
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1(O)cc(O)cc2C(=O)c3cc(C)cc(O)c3C(=O)c12
• Canonical SMILES: Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O
• InChI: InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
• InChIKey: RHMXXJGYXNZAPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: emodin; 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione
• Synonyms: 6-methyl-1,3,8-trihydroxyanthraquinone; Emodin; 3-METHYL-1,6,8-TRIHYDROXYANTHRAQUINONE; 1,3,8-Trihydroxy-6-methylanthraquinone; 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione; 1,3,8-Tri-hydroxy-6-methyl-anthra-quinone; 6-Methyl-1,3,8-tri-hydroxy-anthra-quinone; Emodol; Frangula-emodin; Emodin; Rheum-emodin; Frangula emodin; Archin; Frangulinic acid; Alatinone

Database IDs

• CAS Number: 60529-33-1; 518-82-1
• EC Number: 208-258-8
• MDL Number: MFCD00001207
• Beilstein Number: 1888141
• PubChem SID: 24278164; 24868646; 99444186; 160968782
• PubChem CID: 3220
• CHEBI ID: 42223
• CHEMBL: 289277
• Chemspider ID: 3107
• DrugBank ID: DB07715
• KEGG ID: C10343
• Unique Ingredient Identifier: KA46RNI6HN
• Wikipedia Title: Emodin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.2862926
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.8144279
• LogD (pH = 7.4): 3.4330437
• Log P: 3.8214314
• Molar Refractivity: 72.1349 cm^3
• Polarizability: 26.917091 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.66
• LOG S: -3.09
• Solubility (Water): 2.22e-01 g/l

PROPERTIES

Physical Property

• Solubility: aqueous base: soluble; DMSO: soluble; ethanol: soluble
• Apperance: Yellow powder
• Melting Point: 253-257 °C; 255°C (decomposes)

Safety Information

• Storage Condition: -20°C; 2-8°C
• RTECS: CB7920600
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CSNK2A1(1457), CSNK2B(1460), ELA2(1991), NFKB1(4790), NKAP(79576), NKRF(55922); human ... ELA2(1991)
• Mechanism of Action: Inhibitor of phosphoinositide- 3-kinase (PI3K)/AKT; Monoamine oxidase inhibitor

Product Information

• Purity: ≥95%; ~98%; ≥90% (HPLC); ≥97.0% (HPLC); 99.0
• Grade: analytical standard
• Salt Data: Free Base
• Impurities: ≤5.0% water
• Biological Source: from Frangula bark; Present in Cascara sagrada, in aloes and in other plant material. Isol. from Penicillium spp., Aspergillus spp. and from Anixiella micropetrusa
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antimicrobial; Antineoplastic agent; Cathartic agent
• Empirical Formula (Hill Notation): C15H10O5

DETAILS

MP Biomedicals - 02190453

From Frangula Bark
Purity: ~98%
A protein tyrosine kinase inhibitor.

MP Biomedicals - 02199021

Purity:>95% (HPLC)

MP Biomedicals - 05206347

MP Biomedicals Rare Chemical collection

DrugBank - DB07715

Drug information: experimental

Selleck Chemicals - S2295

Research Area: Inflammation
Biological Activity:
Emodin is a purgative resin, 6-methyl-1,3,8-trihydroxyanthraquinone, from rhubarb, the buckthorn and Japanese Knotweed (Fallopia japonica). It belongs to a family of compounds called anthraquinones, which have shown anti-inflammatory and anticancer effects. [1][2]

Sigma Aldrich - E7881

Biochem/physiol Actions
Inhibitor of NF-κB activation and adhesion molecule expression. Casein Kinase 2 (CK2) inhibitor.
Packaging
50, 250 mg in poly bottle

REFERENCES

• http://www.cancer.gov/dictionary/?CdrID=330167
• Anderson, J.A. et al., Phytochemistry, 1986, 25, 1115, (biosynth)
• Ahmed, S.A. et al., Chem. Comm., 1987, 883, (synth)
• Kalidhar, S.B., Phytochemistry, 1989, 28, 2455; 3459, (pmr)
• Coskun, M. et al., Phytochemistry, 1990, 29, 2018, (cd, pmr, cmr)
• Schmidt, R.R. et al., Synthesis, 1994, 255, (synth, pmr)
• Wang, E.-C. et al., Heterocycles, 1996, 43, 969, (isol, uv, ir, pmr, cmr, ms)
• Fujimoto, H. et al., Chem. Pharm. Bull., 1998, 46, 1506-1510, (isol, activity)
• Francis, G.W. et al., Magn. Reson. Chem., 1998, 36, 769-772, (pmr, cmr, Frangulins, Glucofrangulins)
• Macias, M. et al., J. Nat. Prod., 2000, 63, 757-761, (Emodin, activity)
• Sigma-Aldrich Library of Stains, Dyes and Indicators, 298
• Cole, R.J. et al., Handbook of Toxic Fungal Metabolites, Academic Press, New York, 1981, 684
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MQF250
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91D, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 88D, (ir)
• Eder, R. et al., Helv. Chim. Acta, 1925, 8, 140, (bibl)
• Steglich, W. et al., Chem. Ber., 1972, 105, 2928
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1265; 1274, (occur)
• Wagner, H., Tet. Lett., 1972, 5013
• Hrhammer, H.P. et al., Z. Naturforsch., B, 1972, 27, 959
• Okabe, H., Chem. Pharm. Bull., 1973, 21, 1254
• Hirose, Y. et al., Chem. Pharm. Bull., 1973, 21, 2790, (synth)
• Hassall, C.H. et al., J.C.S. Perkin 1, 1973, 2853, (synth, derivs)
• Banville, J. et al., Can. J. Chem., 1974, 52, 80, (synth, uv, ir, pmr)
• Banville, J. et al., J.C.S. Perkin 1, 1976, 1852
• Fairbairn, J.W., Pharmacology, Suppl. 1, 1976, 14, 1, (rev)
• Kelly, T.R. et al., J.O.C., 1983, 48, 3573, (isol)