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1162-65-8

Basic Information
CAS No.: 1162-65-8
Name: AFLATOXIN B1
Article Data: 7
Molecular Structure:
Molecular Structure of 1162-65-8 (AFLATOXIN B1)
Formula: C17H12O6
Molecular Weight: 312.279
Synonyms: 1-Cyclopentene-1-carboxylicacid, 2-(3a,8a-dihydro-4-hydroxy-6-methoxyfuro[2,3-b]benzofuran-5-yl)-5-oxo-, d-lactone (7CI);Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,9a-tetrahydro-4-methoxy-, (6aR,9aS)- (9CI);Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione,2,3,6a,9a-tetrahydro-4-methoxy-, (6aR-cis)-;Cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione, 2,3,6aa,9aa-tetrahydro-4-methoxy- (8CI);(-)-Aflatoxin B1;AFB1;NSC 529592;Aflatoxin B1;
EINECS: 214-603-3
Density: 1.56g/cm3
Melting Point: 268-269 °C
Boiling Point: 528.2°C at 760 mmHg
Flash Point: 2 °C
Solubility: 15mg/L(temperature not stated)
Appearance: solid
Hazard Symbols: VeryT+, ToxicT, HarmfulXn, FlammableF
Risk Codes: 45-46-26/27/28-36-20/21/22-11-65-48/23/24/25-36/38-39/23/24/25-23/24/25
Safety: 53-45-36-26-16-24-7
Transport Information: UN 3462 6.1/PG 1
PSA: 74.97000
LogP: 2.27650
Synthetic route
Conditions
ConditionsYield
Stage #1: aflatoxin B2a With acetic anhydride; acetic acid at 20℃; for 20h;
Stage #2: In toluene at 240℃; for 0.25h; Further stages.;
24%
30361-73-0, 17878-69-2

O-methylsterigmatocystin

1162-65-8

aflatoxin B1

Conditions
ConditionsYield
With NADPH In acetone at 37℃; for 84h; cell free extract of the Aspergillus parasiticus mutant AVN-1 (ATCC 56774);
10254-99-6

norsolorinic acid

1162-65-8

aflatoxin B1

Conditions
ConditionsYield
With metabolite-free SU-1 cell-free extract; S-Adenosylmethionine; NADPH; flavin adenine dinucleotide In water at 30℃; for 8h;
10048-13-2

sterigmatocystin

1162-65-8

aflatoxin B1

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / K2CO3 / acetone / Heating
2: NADPH / acetone / 84 h / 37 °C / cell free extract of the Aspergillus parasiticus mutant AVN-1 (ATCC 56774)
View Scheme
1162-65-8

aflatoxin B1

d2-aflatoxin B2

Conditions
ConditionsYield
With deuterium In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; under 750.075 Torr;93%
1162-65-8

aflatoxin B1

A

52373-83-8

aflatoxin D1

B

412338-95-5

6-Methoxy-3a,8a-dihydro-benzo[b]furo[3,2-d]furan-4-ol

Conditions
ConditionsYield
With ammonium hydroxide at 50℃; for 504h;A 57%
B 9%
With ammonium hydroxide at 52℃; for 28h; Product distribution;
79-21-0

peracetic acid

1162-65-8

aflatoxin B1

79971-09-8

<6aS-(6aα,8β,9aα)>-8,9-bis(acetyloxy)-2,3,6a,8,9,9a-hexahydro-4-methoxycyclopentafuro<3',2':4,5>furo<2,3-h>benzopyran-1,11-dione

Conditions
ConditionsYield
In dichloromethane; benzene at 25℃; for 15h;34%
1162-65-8

aflatoxin B1

79971-08-7

3',5'-O-dibutyryl 2'-deoxyguanosine

A

17878-54-5

aflatoxin B2a

B

50668-79-6

050668-79-6

C

63425-04-7

<6aS-(6aα,8bβ,9α,9aα)>-8-(2-amino-1,6-dihydro-6-oxo-7H-purin-7-yl)-2,3-6a,8,9,9a-hexahydro-9-hydroxy-4-methoxycyclopentafuro<3',2':4,5>furo<2,3-h><1>benzopyran-1,11-dione

Conditions
ConditionsYield
With benzil In 1,2-dichloro-benzene at 100℃; for 1h; Irradiation;A 14%
B n/a
C 19%
1162-65-8

aflatoxin B1

A

17878-54-5

aflatoxin B2a

B

50668-79-6

050668-79-6

C

63425-04-7

<6aS-(6aα,8bβ,9α,9aα)>-8-(2-amino-1,6-dihydro-6-oxo-7H-purin-7-yl)-2,3-6a,8,9,9a-hexahydro-9-hydroxy-4-methoxycyclopentafuro<3',2':4,5>furo<2,3-h><1>benzopyran-1,11-dione

Conditions
ConditionsYield
With 2'-deoxyguanosine di-n-butyrate; benzil In 1,2-dichloro-benzene at 100℃; for 1h; Irradiation;A 14%
B n/a
C n/a
1162-65-8

aflatoxin B1

74087-85-7

3,3-dimethyldioxirane

42583-46-0

Aflatoxin B1 8,9-epoxide

Conditions
ConditionsYield
In dichloromethane; acetone for 0.25h; Ambient temperature;
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Consensus Reports

IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 83.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 10 (1976),p. 51.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 (1972),p. 145.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Specification

The Aflatoxin B1, with the CAS registry number 1162-65-8,is also known as Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-4-methoxy-. It belongs to the product categories of Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals. Its EINECS number is 214-603-3. This chemical's molecular formula is C17H12O6 and molecular weight is 312.27. What's more,Its systematic name is Aflatoxin B1.It is a potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1. In addition, Aflatoxin B1 (CAS NO.1162-65-8) is sensitive with air and light. It is not compatible with strong oxidizing agents, acids, alkalies, and you must not take it with dust generation, direct sunlight and incompatible materials and not be exposured to air. And also prevent it to broken down into hazardous decomposition products: carbon dioxide, carbon monoxide.

Physical properties about Aflatoxin B1 are:
(1)ACD/LogP:  2.039; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  2.04; (4)ACD/LogD (pH 7.4):  2.04; (5)ACD/BCF (pH 5.5):  20.87; (6)ACD/BCF (pH 7.4):  20.87; (7)ACD/KOC (pH 5.5):  306.29; (8)ACD/KOC (pH 7.4):  306.29; (9)#H bond acceptors:  6; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  1; (12)Index of Refraction:  1.687; (13)Molar Refractivity:  76.011 cm3; (14)Molar Volume:  199.584 cm3; (15)Polarizability:  30.133 10-24cm3 ; (16)Surface Tension:  68.7190017700195 dyne/cm; (17)Density:  1.565 g/cm3; (18)Flash Point:  237.669 °C; (19)Enthalpy of Vaporization:  80.29 kJ/mol; (20)Boiling Point:  528.151 °C at 760 mmHg; (21)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C5C=4C(=O)Oc3c1c(OC2O\C=C/C12)cc(OC)c3C=4CC5;
(2)Std. InChI:InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3;
(3)Std. InChIKey:OQIQSTLJSLGHID-UHFFFAOYSA-N.

Safety Information of Aflatoxin B1:
Risk Statements:(1)Highly flammable; (2)Harmful by inhalation, in contact with skin and if swallowed; (3)Toxic by inhalation, in contact with skin and if swallowed; (4)Very toxic by inhalation, in contact with skin and if swallowed; (5)Irritating to eyes and skin; (6)Danger of very serious irreversible effects; (7)May cause cancer; (8)May cause heritable genetic damage; (9)Harmful: may cause lung damage if swallowed.
Safety Statements:(1)Keep container tightly closed; (2)Keep away from sources of ignition; (3)Avoid contact with skin; (4)In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; (5)Wear suitable protective clothing; (6)In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible; (7)Avoid exposure - obtain special instructions before use

The toxicity data of Aflatoxin B1 are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 550ug/kg (0.55mg/kg) LIVER: OTHER CHANGES Cancer Research. Vol. 29, Pg. 236, 1969.
cat LD50 unreported 550ug/kg (0.55mg/kg)   Japanese Journal of Toxicology. Vol. 2, Pg. 377, 1989.
chicken LD50 unreported 6300ug/kg (6.3mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1327, 1981.
dog LD50 unreported 500ug/kg (0.5mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1327, 1981.
dog LDLo intraperitoneal 1mg/kg (1mg/kg)   Pathologia Veterinaria. Vol. 3, Pg. 331, 1966.
domestic animals - goat/sheep LD50 unreported 1mg/kg (1mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1327, 1981.
domestic animals - goat/sheep LDLo oral 2mg/kg (2mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Nature. Vol. 225, Pg. 1062, 1970.
duck LD50 oral 335ug/kg (0.335mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 123, Pg. 151, 1966.
duck LD50 unreported 335ug/kg (0.335mg/kg)   Japanese Journal of Toxicology. Vol. 2, Pg. 377, 1989.
guinea pig LD50 intraperitoneal 1400ug/kg (1.4mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
LIVER: OTHER CHANGES
Journal of Pathology and Bacteriology. Vol. 91, Pg. 277, 1966.
guinea pig LD50 oral 2mg/kg (2mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 169, 1971.
guinea pig LD50 unreported 1400ug/kg (1.4mg/kg)   Toxicon. Vol. 18, Pg. 121, 1980.
hamster LD50 intraperitoneal 6mg/kg (6mg/kg)   Archives of Pathology. Vol. 83, Pg. 53, 1967.
hamster LD50 oral 10mg/kg (10mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
LIVER: MULTIPLE EFFECTS
Cancer Research. Vol. 29, Pg. 236, 1969.
hamster LD50 unreported 10200ug/kg (10.2mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1327, 1981.
monkey LD50 oral 2200ug/kg (2.2mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
BEHAVIORAL: FOOD INTAKE (ANIMAL)
Toxicology and Applied Pharmacology. Vol. 19, Pg. 169, 1971.
monkey LD50 unreported 7800ug/kg (7.8mg/kg)   Japanese Journal of Toxicology. Vol. 2, Pg. 377, 1989.
monkey LDLo intraperitoneal 1300ug/kg (1.3mg/kg) LIVER: OTHER CHANGES American Journal of Pathology. Vol. 49, Pg. 1023, 1966.
mouse LD50 intraperitoneal 9500ug/kg (9.5mg/kg)   Life Sciences, Part 1: Physiology and Pharmacology. Vol. 13, Pg. 1143, 1973.
mouse LD50 oral 9mg/kg (9mg/kg)   Annual Review of Phytopathology. Vol. 12, Pg. 303, 1974.
pig LD50 oral 620ug/kg (0.62mg/kg)   Annual Review of Phytopathology. Vol. 12, Pg. 303, 1974.
pig LD50 unreported 6600ug/kg (6.6mg/kg)   Japanese Journal of Toxicology. Vol. 2, Pg. 377, 1989.
rabbit LD50 oral 400ug/kg (0.4mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) American Journal of Veterinary Research. Vol. 43, Pg. 1027, 1982.
rabbit LD50 unreported 300ug/kg (0.3mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1327, 1981.
rat LD50 intraperitoneal 6mg/kg (6mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 458, 1973.
rat LD50 oral 4800ug/kg (4.8mg/kg)   Cancer Research. Vol. 27, Pg. 2370, 1967.
rat LD50 unreported 6mg/kg (6mg/kg)   Toxicon. Vol. 18, Pg. 121, 1980.