Embelin
Basic information
- CAS
550-24-3- Standard SMILES
CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O- InChIKey
IRSFLDGTOHBADP-UHFFFAOYSA-N- Molecular formula
- C17H26O4
- Average molar mass
- 294.4 g/mol
- Monoisotopic mass
- 294.18310931
Overview
Embelin is a member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease. It has a role as an antimicrobial agent, an antineoplastic agent, a hepatitis C protease inhibitor and a plant metabolite.
Names & identifiers
- Preferred name
- Embelin
- IUPAC
- 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
- English name
- EMBELIN
- Molecular formula
- C17H26O4
- Molecular weight
- 294.39
Names & synonyms
EMBELIN550-24-3Embelic acidEmberine2,5-Dihydroxy-3-undecyl-1,4-benzoquinone2,5-Dihydroxy-3-undecyl-p-benzoquinone2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dioneSHC6U8F5ERCHEBI:4778p-Benzoquinone, 2,5-dihydroxy-3-undecyl-DTXSID80203537NSC-91874
Show more names
NSC 91874Embelin-RMembelicacidEmbelin, >98%XIAP INHIBITOREMbeliaquinoneEmbelin (Standard)TIMTEC-BB SBB005949
RefChem:136587DTXCID10126028208-979-82,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dioneMFCD00016369NSC918742,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl-2,5-Dihydroxy-3-undecyl-[1,4]benzoquinone
Database identifiers
- CAS
550-24-3- PubChem CID
- 3218
- DTXSID
DTXSID80203537
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 10
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 432
Experimental & physicochemical properties
LipidsLipids -> Polyketides [PK] -> Phenolic lipids [PK15] -> Alkyl hydroquinones and derivatives [PK1505]
Physicochemical properties
- Melting point
- 142 · 142-143°C
- Boiling point
- 356.15 °C · 356.15°C (rough estimate)
- Density
- 1.131 · 1.131
- refractive index
- 1.423 · 1.4230 (estimate)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 10 mg/mL · DMSO: >10 mg/mL
- form
- solid
- pka
- 2.84 · 2.84±0.50(Predicted)
- color
- Dark orange
- Sensitive
- Light Sensitive
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
- InChI
- 1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
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
H361 (75%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P273, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesRepr. 2 (75%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- DK4230000
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361f
- Hazard Classifications
- Repr. 2
- Precautionary statements
- P201-P308+P313
Chemistry & industry
Applications
DescriptionEmbelin (550-24-3) inhibitsthe lysine acetyl transferase PCAFin vitro and in vivo(in vitroIC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1 Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3Possesses anti-inflammatory and analgesic activityin vivo.4Cell-permeable.
UsesEmbelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embelin also displays contraceptive and pro-apoptotic properties.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an ineoplastic and inhibitory activity towards hepatitis C protease.
Related reactions
1 records
Compound notes
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