S-Bioallethrin

Names

[ Name ]:
S-Bioallethrin

[Synonym ]:
(S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
(1S)-2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl (1R,3R)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate
S-bioallethrin
EINECS 249-013-5
(1S)-2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
(S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R)-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
esdépalléthrine
esdepallethrine

Biological Activity

[Description]:

S-Bioallethrin is a pyrethroid insecticide. S-Bioallethrin disrupts nerve function by modifying the gating kinetics of transitions between the conducting and nonconducting states of voltage-gated sodium channels[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Neurological Disease

[References]

[1]. McCavera SJ, et al. Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin. Neurotoxicology. 2012;33(3):384-390.

Chemical & Physical Properties

[ Density]:
1.05 g/cm3

[ Boiling Point ]:
386.8ºC at 760 mmHg

[ Melting Point ]:
49.5ºC

[ Molecular Formula ]:
C₁₉H₂₆O₃

[ Molecular Weight ]:
302.40800

[ Flash Point ]:
166ºC

[ Exact Mass ]:
302.18800

[ PSA ]:
43.37000

[ LogP ]:
4.00200

[ Vapour Pressure ]:
3.46E-06mmHg at 25°C

[ Index of Refraction ]:
1.505 (25ºC)

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GZ1472000

CHEMICAL NAME :: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, (+)-(E)-, ester with (+)- 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one

CAS REGISTRY NUMBER :: 28434-00-6

BEILSTEIN REFERENCE NO. :: 2059862

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C19-H26-O3

MOLECULAR WEIGHT :: 302.45

WISWESSER LINE NOTATION :: L5V BUTJ B2U1 C1 DOV- BL3TJ A1 A1 C1UY1&1

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 :: 430 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - chromodacryorrhea Behavioral - excitement Behavioral - ataxia

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 14,15,1976

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 mg/m3/3H

TOXIC EFFECTS :: Behavioral - excitement Behavioral - ataxia Kidney, Ureter, Bladder - other changes

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 14,15,1976

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 25 gm/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1315,1984

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - excitement Behavioral - ataxia

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 14,15,1976

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2720 mg/m3/3H

TOXIC EFFECTS :: Behavioral - excitement Behavioral - ataxia Kidney, Ureter, Bladder - other changes

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 14,15,1976

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2600 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 28,1451,1977

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1545 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,78,1991

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,78,1991

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 1700 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - excitement Behavioral - ataxia

REFERENCE :: PCBPBS Pesticide Biochemistry and Physiology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1971- Volume(issue)/page/year: 20,217,1983 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302 + H312-H330-H410

[ Precautionary Statements ]:
P260-P280-P301 + P312 + P330-P304 + P340 + P310-P403 + P233

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn: Harmful;N: Dangerous for the environment;

[ Risk Phrases ]:
R20/22

[ Safety Phrases ]:
36-60-61

[ RIDADR ]:
UN3082 9/PG 3

[ RTECS ]:
GZ1472000

[ Packaging Group ]:
I; II; III

[ Hazard Class ]:
6.1

[ HS Code ]:
2918300016

Customs

[ HS Code ]: 2918300016

Articles

Influence of pyrethroids and piperonyl butoxide on histamine release from isolated rat mast cells.

Inflamm. Res. 56(11) , 473-8, (2007)

Pyrethroids are insecticides with low acute toxicity in mammals but their world-wide use for domestic and occupational purposes has caused concern about the risks of long-term exposure. The mammalian ...

The effects of combined exposure to the pyrethroids deltamethrin and S-bioallethrin on hippocampal inhibition and skeletal muscle hyperexcitability in rats.

Toxicol. Appl. Pharmacol. 216(2) , 354-62, (2006)

The default assumption that different pyrethroid insecticides, sharing a common mode of action, will show additivity of toxicity has not always been supported by in vitro measures, some of which have ...

Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin

Neurotoxicology 33(3) , 384-90, (2012)

Highlights ► We constructed Nav1.6Q3 sodium channels containing the IFM/QQQ mutation. ► Nav1.6Q3 channels expressed in Xenopus oocytes exhibited persistent activation. ► Opening of Nav1.6Q3 channels e...