HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke

HCID 98608Erstellt: 1. November 2026

Phellopterin

phelloptorin · NSC 152469 · PHELLOPTERIN(P) · Phellopterin-RM · phellopterin USP/EP/BP · Phellopterin (Standard) · Phellopterin, 10 mM in DMSO · 4-Methoxy-9-prenyloxypsoralen

https://huagongshe.com/de/chemical/98608

Identifikatoren & physikalische Daten

CAS No.	2543-94-4
Summenformel	C17H16O5
Durchschnittliche Molmasse	300,3 g/mol
Monoisotopische Masse	300,09977361 g/mol
SMILES	COc1c2ccoc2c(OCC=C(C)C)c2oc(=O)ccc12
InChIKey	BMLZFLQMBMYVHG-UHFFFAOYSA-N
PubChem CID	98608
ChEMBL	CHEMBL452751
ChEBI	CHEBI:80887
EC No.	110-046-4
DTXSID	DTXSID30180086

Chemische & physikalische Eigenschaften

XLogP	3,8
Polarare Oberfläche (TPSA)	57,9
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	5
Frei drehbare Bindungen	4
Schwere Atome	22
Formalladung	0
Komplexität	479
SpringerMaterials Properties	Chemical shift
LogP (Verteilungskoeffizient)	3.86
Schmelzpunkt	102-103℃
Siedepunkt	480.4±45.0 °C(Predicted)
Dichte	1.243
Lagerbedingungen	Store at -20°C
Löslichkeit	Soluble in acetonitrile and chloroform
Aggregatzustand	powder
Farbe	Light yellow
Hauptanwendungen	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
LogP (Verteilungskoeffizient)	2.867 (est)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (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 Classes and Categories	Acute Tox. 4 (100%)
Gesundheitliche Auswirkungen	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)
Toxizitätsübersicht	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)
Carcinogen Classification	Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135)

CAS No.

2543-94-4

Summenformel

C17H16O5

Durchschnittliche Molmasse

300,3 g/mol

Monoisotopische Masse

300,09977361 g/mol

SMILES

COc1c2ccoc2c(OCC=C(C)C)c2oc(=O)ccc12

InChIKey

BMLZFLQMBMYVHG-UHFFFAOYSA-N

PubChem CID

98608

ChEMBL

CHEMBL452751

ChEBI

CHEBI:80887

EC No.

110-046-4

DTXSID

DTXSID30180086

Chemische & physikalische Eigenschaften

XLogP

3,8

Polarare Oberfläche (TPSA)

57,9

H-Brücken-Donoren

H-Brücken-Akzeptoren

Frei drehbare Bindungen

Schwere Atome

Formalladung

Komplexität

479

SpringerMaterials Properties

Chemical shift

LogP (Verteilungskoeffizient)

3.86

Schmelzpunkt

102-103℃

Siedepunkt

480.4±45.0 °C(Predicted)

Dichte

1.243

Lagerbedingungen

Store at -20°C

Löslichkeit

Soluble in acetonitrile and chloroform

Aggregatzustand

powder

Farbe

Light yellow

Hauptanwendungen

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

LogP (Verteilungskoeffizient)

2.867 (est)

Sicherheit & Vorschriften

GHS-Einstufung

WarningH302 (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 Classes and Categories

Acute Tox. 4 (100%)

Gesundheitliche Auswirkungen

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)

Toxizitätsübersicht

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)

Carcinogen Classification

Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135)