Emodin

Emodin
Compound Structure:
Synonyms: 1,3,8-trihydroxy-6-methylanthracene-9,10-dione; 1,3, 8-Trihydroxy-6-methyl-9,10-anthraquinone; 1,3,8-Trihydroxy-6-methyl-9,10-anthraquinone; 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione; 1,3,8-Trihydroxy-6-methylanthra-9,10-quinone
Compound ID: NMPC-1004
PubChem ID:

3220

Molecular Formula: C15H10O5
Canonical SMILES: CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
InChIKey: RHMXXJGYXNZAPX-UHFFFAOYSA-N
About the compound:

Emodin is a trihydroxyanthraquinone, specifically a type of 9,10-anthraquinone, which is substituted with hydroxy groups at positions 1, 3, and 8, and a methyl group at position 6. This compound is found in various natural sources, notably in the roots and barks of plants such as rhubarb and buckthorn, as well as in certain molds and lichens. It's also an active ingredient in a range of Chinese herbal remedies. In the realm of pharmacology, emodin serves multiple roles. It functions as a tyrosine kinase inhibitor, an antineoplastic (anti-cancer) agent, and a laxative. Additionally, it is recognized as a plant metabolite and is functionally related to emodinanthrone. Chemically, emodin is the conjugate acid of an emodin(1-). Emodin has garnered attention in medical research, particularly for its potential in treating Polycystic Kidney disease. As a member of the anthraquinone family, emodin (6-methyl-1,3,8-trihydroxyanthraquinone) can be isolated from plants like rhubarb, buckthorn, and Japanese knotweed (Reynoutria japonica syn. Polygonumcuspidatum). It's particularly abundant in the roots of Chinese rhubarb (Rheum palmatum), as well as in knotweed, knotgrass (Polygonumcuspidatum and multiflorum), and in Hawaii ‘au‘auko‘i cassia seeds or coffee weed (Semen cassia). Its specific isolation is noted from Rheum palmatum L. Moreover, emodin is produced by various fungal species, including those in the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis. Its common name, "emodin," is derived from Rheum emodi, a synonym of Rheum australe (Himalayan rhubarb). Other synonyms for emodin include emodol, frangulaemodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb, and Persian Berry Lake.

GHS Hazard Statements

H315 (94%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (94%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

First Aid

In case of exposure:

EYES: Remove contact lenses, flush with water or saline for 20-30 minutes, seek medical help, transport to hospital immediately.

SKIN: Flood with water, wash with soap, seek medical help if symptoms develop.

INHALATION: Leave contaminated area, seek medical help even without symptoms, provide respiratory protection.

INGESTION: If conscious and not convulsing, give water, call hospital or poison control, consider vomiting induction under certain circumstances with caution, transport to hospital immediately if convulsing or unconscious (NTP, 1992).

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

270.24 g/mol

XLogP3-AA

2.7

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

5

Rotatable Bond Count

0

Exact Mass

270.05282342 g/mol

Monoisotopic Mass

270.05282342 g/mol

Topological Polar Surface Area

94.8Ų

Heavy Atom Count

20

Formal Charge

0

Complexity

434

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Emodin appears as orange needles or powder. (NTP, 1992)

Boiling Point

Sublimes (NTP, 1992)

Melting Point

493 to 495 °F (NTP, 1992)

Solubility 

Practically insoluble in water; soluble in alcohol, aqueous alkali hydroxide solutions (cherry red color), sodium carbonate and ammonia solutions.

Source: PubChem                   

Source Species: Senna occidentalis
Download SDF