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484-20-8

484-20-8 structure
484-20-8 structure
  • Name: Bergapten
  • Chemical Name: 5-methoxypsoralen
  • CAS Number: 484-20-8
  • Molecular Formula: C12H8O4
  • Molecular Weight: 216.189
  • Catalog: Pharmaceutical intermediate Heterocyclic compound Pyran compound
  • Create Date: 2018-06-29 07:58:05
  • Modify Date: 2024-01-02 18:08:15
  • Bergapten is a natural anti-inflammatory and anti-tumor agent isolated from bergamot essential oil, other citrus essential oils and grapefruit juice. Bergapten is inhibitory towards mouse and human CYP isoforms.
Name 5-methoxypsoralen
Synonyms Geralen
Heraclin
Bergapten
EINECS 207-604-5
4-MOP
Bergaptan
MFCD00010272
4-Methoxyfuro[3,2-g]benzopyrane-7-one,5-Methoxypsoralen,Bergapten
7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy-
MAJUDIN
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
5-Methoxypsoralen
4-Methoxyfuro[3,2-g]Benzopyran-7-One
5-MOP
5-19-06-00004 (Beilstein Handbook Reference)
4-Methoxy-furo[3,2-g]chromen-7-one
Psoraderm
4-Methoxy-7H-furo[3,2-g]chromen-7-one
Description Bergapten is a natural anti-inflammatory and anti-tumor agent isolated from bergamot essential oil, other citrus essential oils and grapefruit juice. Bergapten is inhibitory towards mouse and human CYP isoforms.
Related Catalog
Target

CYP[1]

In Vitro There is decreased N-acetyltransferase (NAT) activity in SC-M1 cells at concentrations of Bergapten (5-Methoxypsoralen, 5-MOP) from 0.05 mM to 25 mM, but no obvious dose-dependent effect is found between these doses (r=0.5687). In COLO 205 cells, there is decreased NAT activity at low doses of Bergapten (0.05 mM and 0.5 mM) and increased NAT activity at a high dose (50 mM). Bergapten induces a dosedependent effect in our experimental concentrations on COLO 205 cells (r=0.8912); a promotion effect at a higher dose (50 mM) and an inhibition effect at lower doses (0.05-0.5 mM), while the concentrations 5-25 mM has no significant difference compared with the control regimen[1]. Bergapten (5-Methoxypsoralen) exerts inhibitory effects on diabetes-related osteoporosis via the regulation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways in osteoprotegerin knockout mice. Bergapten has also been shown to significantly inhibit the production of pro-inflammatory cytokines. Bergapten exhibits the ability to significantly inhibit RANKL-RANK signaling transduction, and to suppress the activation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways, thus protecting trabecular structure and decreasing osteoclastogenic differentiation[2].
In Vivo The metabolic activity of NAT of the rat colon is higher than that of the stomach, and Bergapten (5-Methoxypsoralen, 5-MOP) causes a decrease of AF concentration in the stomach at the 24-h time-period. The concentrations of AAF in the stomach and colon are low. Although DMSO (solvent) influenced the metabolism of AAF, compared with the control regimen, Bergapten still causes an increase in the further metabolism of AAF, and a decrease in the concentration of AAF in the stomach at 24 h, and in the colon during the 24- to 72-h time-period[1].
Cell Assay The human colon adenocarcinoma cell line (COLO 205, from a 70-year-old male Caucasian) sre placed into 75-cm2 tissue culture flasks and grown in RPMI1640 medium, supplemented with 10% fetal bovine serum, containing penicillin and streptomycin (100 μg/mL) and 1 mM glutamine, at 37°C in a humidified atmosphere of 5% CO2 and 95% O2. The human stomach adenocarcinoma cell line are placed into 75-cm2 tissue culture flasks and grown in RPMI 1640 medium, supplemented with 10% fetal bovine serum, containing penicillin and streptomycin (100 μg/mL) and 1 mM glutamine, at 37°C in a humidified atmosphere of 5% CO2 and 95% O2. SC-M1 and COLO 205 cells are treated with different concentrations of Bergapten (0.05, 0.5, 5, 10, 25 and 50 mM) and incubated for 72 h for the dose-effect study of Bergapten on NAT activity. To determine the time-course effect of 0.5 mM Bergapten on NAT activity, the cells are incubated at 37AC and harvested at 12, 24, 48 and 72 h, respectively. Bergapten is dissolved in DMSO and the final concentration of vehicle is <0.1%. Only DMSO (solvent) is added for the control regimen[1].
Animal Admin Rats[1] Seventy-two male Sprague-Dawley (SD) rats, weighing approximately 200 g are used. A total of 72 rats are subjected to 3 different regimens, each regimen divided into 4 groups with 6 rats in each group. Gastric intubation is used for delivery of the test compounds into each animal. The first regimen received 1 mL Bergapten (dissolved in DMSO) at a dose of 0.5 mmol per Kg of body weight. Regimen 2, the control regimen, received only 1 mL solvent (DMSO), without any Bergapten. Regimen 3, the contrast regimen, received nothing at that time. Twenty-four h later, all of the rats from the 3 regimens received 1mL AF (dissolved in DMSO) at a dose of 0.3 mmol per Kg of body weight. The groups are divided by different collecting time: 12, 24, 48 and 72 h after AF administration, and then the animals are transferred to individual metabolism cages. The stomachs and the colons of the rats from each regimen are collected and are immediately extracted with ethyl acetate/methanol (95:5). The solvent is evaporated and the residue redissolved in methanol and assayed for AF and AAF by HPLC.
References

[1]. Lee YM, et al. Effects of 5-methoxypsoralen (5-MOP) on arylamine N-acetyltransferase activity in the stomach and colon of rats and human stomach and colon tumor cell lines. In Vivo. 2005 Nov-Dec;19(6):1061-9.

[2]. Li XJ, et al. Bergapten exerts inhibitory effects on diabetes-related osteoporosis via the regulation of the PI3K/AKT, JNK/MAPK and NF-κB signaling pathways in osteoprotegerin knockout mice. Int J Mol Med. 2016 Dec;38(6):1661-1672.
Density 1.4±0.1 g/cm3
Boiling Point 412.4±45.0 °C at 760 mmHg
Melting Point 190-193 °C(lit.)
Molecular Formula C12H8O4
Molecular Weight 216.189
Flash Point 203.2±28.7 °C
Exact Mass 216.042252
PSA 52.58000
LogP 2.00
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.635
Storage condition 2-8°C
Stability Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LV1300000
CHEMICAL NAME :
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-methoxy-
CAS REGISTRY NUMBER :
484-20-8
BEILSTEIN REFERENCE NO. :
0019560
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C12-H8-O4
MOLECULAR WEIGHT :
216.20
WISWESSER LINE NOTATION :
T C566 DO LVOJ HO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>30 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
9 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
204 gm/kg/52W-I
TOXIC EFFECTS :
Behavioral - fluid intake Endocrine - evidence of thyroid hyperfunction Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
800 mg/kg/8D-I
TOXIC EFFECTS :
Behavioral - sleep Behavioral - food intake (animal) Skin and Appendages - dermatitis, irritative (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
4368 mg/kg/13W-I
TOXIC EFFECTS :
Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5600 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6720 mg/kg
SEX/DURATION :
female 7-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
900 mg/kg
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 25,302,1995 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,242,1987 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,327,1986 IARC Cancer Review:Group 2A IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,242,1987
Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H334-H340-H350
Precautionary Statements P201-P261-P308 + P313
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes Xi: Irritant;
Risk Phrases R43
Safety Phrases S36/37
RIDADR UN 1759
WGK Germany 2
RTECS LV1300000
HS Code 2932999099
HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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