1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 72916
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c12c(cc(cc1O)CO)C(=O)c1c(C2=O)c(ccc1)O
• Canonical SMILES: OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
• InChIKey: YDQWDHRMZQUTBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione; aloe emodin
• Synonyms: Aloe emodin; 1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione; Aloe-emodin; Aloeemodin; Aloe emodin; 1,8-Dihydroxy-3-hydroxymethylanthraquinone; Aloeemodin; Aloe-emodin; 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione; 3-Hydroxymethylchrysazin; Aloe-emodol; NSC 38628; Rhabarberone; 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone; 3-Hydroxymethylchrysazine; Aloe-emodin

Database IDs

• CAS Number: 481-72-1
• EC Number: 207-571-7
• MDL Number: MFCD00017373
• Beilstein Number: 2059062
• PubChem SID: 162037836; 24891267
• PubChem CID: 10207
• CHEMBL: 40275
• Chemspider ID: 9792
• KEGG ID: C10294
• Wikipedia Title: Aloe_emodin

CALCULATED PROPERTIES

• Acid pKa: 7.8008704
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.842074
• LogD (pH = 7.4): 2.689786
• Log P: 2.8442256
• Molar Refractivity: 71.9287 cm^3
• Polarizability: 26.999968 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Orange Solid; Yellow powder
• Melting Point: 223-224 °C (433.4-435.2°F) (Sublimes in CO₂ stream); 223-224°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: CB6712200
• 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

• Admin Routes: Oral
• Mechanism of Action: Apoptosis inducer; Caspase-3 activator; Caspase-8 activator; Caspase-9 activator;; Protein kinase C (PKC) inhibitor

Product Information

• Purity: ≥95% (HPLC); ≥97.0% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Biological Source: Present in aloe latex, an exudate from the aloe plant
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antibacterial; Antileukaemic; Antimicrobial; Antimutagenic; Antiseptic; Antitumor; Cathartic
• Empirical Formula (Hill Notation): C15H10O5

DETAILS

Selleck Chemicals - S2259

Related research area: Infection

InterBioScreen - BB_NC-2562

Rheum palmatum L.

Sigma Aldrich - A7687

Biochem/physiol Actions
Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

Sigma Aldrich - 93938

Biochem/physiol Actions
Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

Toronto Research Chemicals - A575400

Shows significant inhibitory activity against the P-388 leukemia in mice when administered as a suspension in acetone-Tween 80. Has a specific in vitro and in vivo antineuroectodermal tumor activity. Cathartic.

REFERENCES

• http://en.wikipedia.org/wiki/Aloe_emodin
• Hung, K., et al.: J. Exp. Med., 188, 2357 (1998)
• Gazzola, P.T., et al.: Cancer Res., 60, 2800 (1998)
• Irie, T., et al.: Int. J. Cancer, 121, 8784 (1998)
• Zhao, J., et al.: Eur. J. Neurol., 14, 510 (1998)
• 1. Hatano T, Uebayashi H, Ito H, Shiota S, Tsuchiya T, Yoshida T.
• Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull (Tokyo). 1999 Aug;47(8):1121-7.
• 2. Hofilena, J., Ragasa, C.Y., Rideout, J.A. An antimicrobial and antimutagenic anthraquinone from Cassia alata. ACGC Chemical Research Communications, 2000, 10:15-20.
• 3. Chen SH, Lin KY, Chang CC, Fang CL, Lin CP. Aloe-emodin-induced apoptosis in human gastric carcinoma cells. Food Chem Toxicol. 2007 Nov;45(11):2296-303. Epub 2007 Jun 12.
• 4. Acevedo-Duncan M, Russell C, Patel S, Patel R. Aloe-emodin modulates PKC isozymes, inhibits proliferation, and induces apoptosis in U-373MG glioma cells.
• Int Immunopharmacol. 2004 Dec 20;4(14):1775-84.