Apiole (parsley)

Names

[ CAS No. ]:
523-80-8

[ Name ]:
Apiole (parsley)

[Synonym ]:
Apiole (parsley)
Apiol
1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene
Petersiliencampher
3,6-dimethoxy-4,5-methylenedioxy-allylbenzene
1-allyl-3,4-methylenedioxy-2,5-dimethoxybenzene
Apiole
Apioline
5-Allyl-4,7-dimethoxy-1,3-benzodioxole
Parsley apiol
1,3-Benzodioxole,4,7-dimethoxy-5-(2-propenyl)
Parsley apiole
Parsley camphor

Biological Activity

[Description]:

Apiole is an anti-tumor agent that induces apoptosis and inhibits human colon cancer cells by inducing G0/G1 cell cycle arrest. Apiole also significantly inhibited colon tumor development in an in vivo mouse xenograft model[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[References]

[1]. Wu KH, et al. Study of the antitumor mechanisms of apiole derivatives (AP-02) from Petroselinum crispum through induction of G0/G1 phase cell cycle arrest in human COLO 205 cancer cells. BMC Complement Altern Med. 2019 Jul 27;19(1):188.

[2]. Wei PL, et al. The in vivo antitumor effects on human COLO 205 cancer cells of the 4,7-dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole (apiole) derivative of 5-substituted 4,7-dimethoxy-5-methyl-l,3-benzodioxole (SY-1) isolated from the fruiting body of Antrodia camphorate. J Cancer Res Ther. 2012 Oct-Dec;8(4):532-6.

Chemical & Physical Properties

[ Density]:
1.151g/cm3

[ Boiling Point ]:
294ºC

[ Melting Point ]:
29ºC

[ Molecular Formula ]:
C₁₂H₁₄O₄

[ Molecular Weight ]:
222.24

[ Flash Point ]:
117.2ºC

[ Exact Mass ]:
222.08900

[ PSA ]:
36.92000

[ LogP ]:
2.16100

[ Index of Refraction ]:
1.53

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CY2500000

CHEMICAL NAME :: Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)-

CAS REGISTRY NUMBER :: 523-80-8

BEILSTEIN REFERENCE NO. :: 0195747

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C12-H14-O4

MOLECULAR WEIGHT :: 222.26

WISWESSER LINE NOTATION :: T56 BO DO CHJ FO1 H2U1 IO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 1515 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - other changes

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 5,1613,1984

Safety Information

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36/37/39

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

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%