Angelicin

Names

[ CAS No. ]:
523-50-2

[ Name ]:
Angelicin

[Synonym ]:
2H-Furo[2,3-h][1]benzopyran-2-one
4-Hydroxy-5-benzofuranacrylic acid γ-lactone
Furo[2,3-h]benzopyran-2-one
EINECS 201-480-6
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran,2H-Furo[2,3-h]-1-benzopyran-2-one
ISOPSORALENE
Isopsoralen
ANGELICINE
angecin
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran 2H-Furo[2,3-h]-1-benzopyran-2-one
T B566 EO LVOJ
MFCD00064930
2H-Furo[2,3-h]chromen-2-one
2H-Furo[2,3-h]-1-benzopyran-2-one
isopsoralin
Angelicin
ISOBERGAPTEN

Biological Activity

[Description]:

Angelicin, a furocoumarin naturally occurring tricyclic aromatic compound, structurally related to psoralens, is reported to have anti-cancer, antiviral, anti-inflammatory activity. IC50 value: 49.56 μM (cellular cytotoxicity); 5.39 μg/ml (28.95 μM) (against MHV-68)Target: In vitro: In human SH-SY5Y neuroblastoma cells, angelicin increased cellular cytotoxicity in a dose- and time-dependent manner with IC50 of 49.56 μM at 48 h of incubation. Angelicin dose-dependently downregulated the expression of anti-apoptotic proteins including Bcl-2, Bcl-xL, and Mcl-1; Angelicin-induced apoptosis is mediated primarily through the intrinsic caspase-mediated pathway[1]. Angelicin efficiently inhibited 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced lytic replication of human gammaherpresviruses in both EBV- and KSHV-infected cells [2]. Angelicin was potentially advantageous to prevent inflammatory diseases by inhibiting NF-κB and MAPK pathways [3].In vivo:

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

Natural Products >> Phenylpropanoids

[References]

[1]. Md. Ataur Rahman, Angelicin induces apoptosis through intrinsic caspase-dependent pathway in human SH-SY5Y neuroblastoma cells. Molecular and Cellular Biochemistry October 2012, Volume 369, Issue 1-2, pp 95-104

[2]. Hye-Jeong Cho, et al. Antiviral activity of angelicin against gammaherpesviruses. Antiviral Research Volume 100, Issue 1, October 2013, Pages 75–83

[3]. Fang Liu, et al. Angelicin regulates LPS-induced inflammation via inhibiting MAPK/NF-κB pathways. Journal of Surgical Research Volume 185, Issue 1, November 2013, Pages 300–309

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
362.6±27.0 °C at 760 mmHg

[ Melting Point ]:
132-134ºC

[ Molecular Formula ]:
C₁₁H₆O₃

[ Molecular Weight ]:
186.163

[ Flash Point ]:
173.1±23.7 °C

[ Exact Mass ]:
186.031693

[ PSA ]:
43.35000

[ LogP ]:
2.01

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.667

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV0940000

CHEMICAL NAME :: 2H-Furo(2,3-h)(1)benzopyran-2-one

CAS REGISTRY NUMBER :: 523-50-2

BEILSTEIN REFERENCE NO. :: 0153970

LAST UPDATED :: 199706

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C11-H6-O3

MOLECULAR WEIGHT :: 186.17

WISWESSER LINE NOTATION :: T B566 EO LVOJ

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 :: 322 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Behavioral - analgesia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 165 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Behavioral - analgesia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 254 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Behavioral - analgesia

MUTATION DATA

TYPE OF TEST :: Gene conversion and mitotic recombination

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 100 umol/L

REFERENCE :: BUCABS Bulletin du Cancer. (SPPIF, B.P.22, F-41353 Vineuil, France) V.53- 1966- Volume(issue)/page/year: 67,245,1980 *** REVIEWS *** IARC Cancer Review:Animal 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: 40,291,1986 IARC Cancer Review:Human No Adequate Data 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: 40,291,1986

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312 + H332-H315-H319-H335-H351

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22;R36/37/38;R40

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LV0940000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ 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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