Psoralidin
Basic information
- CAS
18642-23-4- Standard SMILES
CC(C)=CCc1cc2c(cc1O)oc(=O)c1c3ccc(O)cc3oc21- InChIKey
YABIJLLNNFURIJ-UHFFFAOYSA-N- Molecular formula
- C20H16O5
- Average molar mass
- 336.3 g/mol
- Monoisotopic mass
- 336.09977361
Overview
Psoralidin is a member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively. It has a role as an estrogen receptor agonist and a plant metabolite. It is a delta-lactone, a polyphenol and a member of coumestans. It is functionally related to a coumestan.
Names & identifiers
- Preferred name
- Psoralidin
- IUPAC
- 3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
- English name
- psoralidin
- Molecular formula
- C20H16O5
- Molecular weight
- 336.34
Names & synonyms
Psoralidin18642-23-43,9-Dihydroxy-2-prenylcoumestan3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-oneG16ZUQ069LCHEBI:8616DTXSID201719036H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-butenyl)-3,9-dihydroxy-2-(3-methylbut-2-enyl)-(1)benzofuro(3,2-c)chromen-6-oneRefChem:46517DTXCID20943946H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-buten-1-yl)-
Show more names
PsorslidinPsoralidin-RMPsoralidin, BRPsoralidin (6CI)Psoralidin, >=99%Psoralidin (Standard)Psoralidin, 10 mM in DMSO
3-benzofurancarboxylic acid, 2-(2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-6-hydroxy-, delta-lactone683-176-73,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-benzofuro[3,2-c]chromen-6-oneUNII-G16ZUQ069LMFCD10566617BDBM246524HY-N0232NCGC00388431-05
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 79.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 554
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Coumestan flavonoids [PK1209]
Melting Point290 - 292 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 290 · 290-292°
- Boiling point
- 458.8 · 458.8±34.0 °C(Predicted)
- Density
- 1.383 · 1.383±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- 5 mg/mL, · DMSO: soluble5mg/mL, clear (warmed)
- form
- powder
- pka
- 8.7 · 8.70±0.20(Predicted)
- color
- white to beige
- InChI
- 1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
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
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (50%)
Safety data
- wgk
- 3
- hs_code
- 2932.20.4500
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that possess antiestrogenic actions but can also produce estrogenic effects as well. They act as complete or partial agonist or as antagonist. They can be either steroidal or nonsteroidal in structure.
Cellular LocationsMembrane
Applications
DescriptionPsoralidin is a furanocoumarin isolated from the seeds of P. corylifolia, a medicinal plant found in southeastern Asia, that has been shown to induce cytotoxicity against various cancer cells. Through TNF-related apoptosis-inducing ligand-mediated events, psoralidin at 50 μM can induce the death of HeLa cancer cells. It also can induce apoptosis of androgen-dependent (LNCaP, C4-2B) and androgen-independent (DU-145, PC-3) prostate cancer cells and inhibit the growth of PC-3 xenograft tumors in nude mice.
UsesPsoralidin is an antibacterial and antioxidant reagent.
Additional notes
DefinitionChEBI: A member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively.
Related reactions
0 records
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Compound notes
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