Basic information
- CAS
2543-94-4- Standard SMILES
COc1c2ccoc2c(OCC=C(C)C)c2oc(=O)ccc12- InChIKey
BMLZFLQMBMYVHG-UHFFFAOYSA-N- Molecular formula
- C17H16O5
- Average molar mass
- 300.3 g/mol
- Monoisotopic mass
- 300.09977361
Overview
Phellopterin is a member of psoralens.
Names & identifiers
- Preferred name
- Phellopterin
- IUPAC
- 4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
- English name
- phellopterin
- Molecular formula
- C17H16O5
- Molecular weight
- 300.31
Names & synonyms
Phellopterin2543-94-44-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-oneM7UP6XJ2AADTXSID30180086NSC-1524694-METHOXY-9-[(3-METHYLBUT-2-EN-1-YL)OXY]-7H-FURO[3,2-G]CHROMEN-7-ONE4-methoxy-9-(3-methylbut-2-enoxy)furo(3,2-g)chromen-7-one4-methoxy-9-((3-methylbut-2-en-1-yl)oxy)-7H-furo(3,2-g)chromen-7-one4-Methoxy-9-((3-Methylbut-2-En-1-Yl)Oxy)-7H-Furo[3,2-G]Chromen-7-One4-Methoxy-9-((3-methyl-2-buten-1-yl)oxy)-7H-furo(3,2-g)(1)benzopyran-7-one4-Methoxy-9-[(3-methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
Show more names
NSC 152469PHELLOPTERIN(P)Phellopterin-RMphellopterin USP/EP/BPPhellopterin (Standard)Phellopterin, 10 mM in DMSO4-Methoxy-9-prenyloxypsoralenmonocytes,inhibit,VCAM-1,endothelium,Inhibitor,Phellopterin
RefChem:860507DTXCID40102577110-046-4PhelloptorinMLS000574895SMR000156210Phelloterin7H-Furo(3,2-g)(1)benzopyran-7-one, 4-methoxy-9-((3-methyl-2-butenyl)oxy)-
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 57.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 479
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
LogP3.86
Physicochemical properties
- Melting point
- 102 · 102-103℃
- Boiling point
- 480.4 · 480.4±45.0 °C(Predicted)
- Density
- 1.243 · 1.243
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in acetonitrile and chloroform
- form
- powder
- color
- Light yellow
- Major Application
- food and beverages
- InChI
- 1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3
- InChIKey
- BMLZFLQMBMYVHG-UHFFFAOYSA-N
- SMILES
- [o]1c2c(c(c3c([o]cc3)c2OCC=C(C)C)OC)cc[c]1=O
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 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Health Effects
The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. It activates adrenaline-induced lipolysis and activate ACTH-induced lipolysis. (L579)
Toxicity Summary
The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. Phellopterinis also an inhibitor of insect cytochromes P 450. It strongly inhibits the binding of [3H]diazepam to central nervous system benzodiazepine receptors in vitro. (L579)
Chemistry & industry
Applications
DescriptionPhellopterin is a commonly used yin-nourishing medicine in clinical practice. Indications: Dryness of the lungs, dry cough, fever injury, thirst and other symptoms. It is found that the preparation methods of coralline mostly use organic reagent extraction and silica gel column separation.
UsesPhellopterin is a natural product isolated from Angelica dahurica. Phellopterin reduces TNF-alpha-induced VCAM-1 expression through regulation of the Akt and PKC pathway, which contributes to inhibit the adhesion of monocytes to endothelium[1].
Upstream & downstream products
Upstream raw materials
Suppliers100 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…