Aloe emodin
Basic information
- CAS
481-72-1- Standard SMILES
O=C1c2cccc(O)c2C(=O)c2c(O)cc(CO)cc21- InChIKey
YDQWDHRMZQUTBA-UHFFFAOYSA-N- Molecular formula
- C15H10O5
- Average molar mass
- 270.24 g/mol
- Monoisotopic mass
- 270.05282342
Overview
Aloe emodin is a dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe. It has a role as an antineoplastic agent and a plant metabolite. It is an aromatic primary alcohol and a dihydroxyanthraquinone. It is functionally related to a chrysazin.
Names & identifiers
- Preferred name
- Aloe emodin
- IUPAC
- 1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
- English name
- Aloe emodin
- Molecular formula
- C15H10O5
- Molecular weight
- 270.24
Names & synonyms
Aloe-emodinAloe emodin481-72-1AloeemodinRhabarberone3-Hydroxymethylchrysazine1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione3-Hydroxymethylchrysazin1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione1,8-Dihydroxy-3-hydroxymethylanthraquinoneDTXSID2030695
Show more names
RHADiacerein IMpurity BDiacerein impurity B CRSC:C&B63NSC 38628Aloe-eModol
C8IYT9CR7CNSC-38628CHEBI:2607DTXCID0010695RefChem:27157207-571-7Aloe-emodine9,10-Anthracenedione, 1,8-dihydroxy-3-(hydroxymethyl)-
Database identifiers
- CAS
481-72-1- PubChem CID
- 10207
- DTXSID
DTXSID2030695- ChEMBL
CHEMBL40275- ChEBI
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 420
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Anthracenes and phenanthrenes [PK1304]
LogP3.18
Melting Point221 - 223 °C
Physical DescriptionSolid
Collision Cross Section157.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID2030695]
Physicochemical properties
- Melting point
- 223 · 223-224°C
- Boiling point
- 373.35 °C · 373.35°C (rough estimate)
- Density
- 1.328 · 1.3280 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (95.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 9,10-Anthracenedione, 1,8-dihydroxy-3-(hydroxymethyl)-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesSkin Irrit. 2 (95.7%)
Toxicology
Carcinogen Classification
Aloe Vera
TR-553: Photocarcinogenesis Study of Aloe Vera [CASRN 481-72-1 (Aloe-emodin)] in SKH-1 Mice (Simulated Solar Light and Topical Application Study) (2010 )
02/27/08
These experiments investigated the potential of topical application of creams containing extracts of Aloe barbadensis Miller plant (aloe gel, whole leaf, or decolorized whole leaf) or aloe-emodin to alter the photocarcinogenic activity of filtered xenon arc simulated solar light (SSL) in male and female SKH-1 hairless mice. Data on skin lesions were collected both on digital images during the in-life phase and by histopathologic evaluation at necropsy. No effects of creams upon SSL-induced skin lesions were identified from data collected during the in-life phase.
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesAloe-emodin has been used as a standard in high performance liquid chromatography (HPLC) for separation and identification of phenolic compounds in Aloe arborescens Miller var. natalensis Berger (Kidachi aloe).
UsesAloe-emodin may be used as an analytical reference standard for the determination of the analyte in plant and animal samples by high-performance liquid chromatography technique.
UsesShows 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.
General DescriptionDiacerein is known to be a suitable drug to treat osteoarthritis and prevent vascular diseases. It is a semi-synthetic anthraquinone derivative which acts by inhibiting the production of interleukin-1 and secretion of metalloproteases.
Upstream & downstream products
Upstream raw materials
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Compound notes
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