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Dihydroaflatoxin G1

HCID 23670
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
7241-98-7
Standard SMILES
COc1cc2c(c3oc(=O)c4c(c13)CCOC4=O)C1CCOC1O2
InChIKey
WPCVRWVBBXIRMA-UHFFFAOYSA-N
Molecular formula
C17H14O7
Average molar mass
330.29 g/mol
Monoisotopic mass
330.07395278

Overview

Dihydroaflatoxin G1 has been reported in Aspergillus flavus with data available.

Names & identifiers

Preferred name
Dihydroaflatoxin G1
IUPAC
11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.02,9.03,7.013,18]icosa-1,9,11,13(18)-tetraene-17,19-dione
English name
AFLATOXIN G2
Molecular formula
C17H14O7
Molecular weight
330.29

Names & synonyms

Dihydroaflatoxin G11H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a,9,10,10a-hexahydro-5-methoxy-, (7aR-cis)-1H,12H-Furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione, 3,4,7a.alpha.,9,10,10a.alpha.-hexahydro-5-methoxy-SCHEMBL935567orb1708070WPCVRWVBBXIRMA-UHFFFAOYSA-N11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.02,9.03,7.013,18]icosa-1,9,11,13(18)-tetraene-17,19-dioneLS-14556NS00000081T135335-Methoxy-3,4,7a,9,10,10a-hexahydro-1H,12H-furo[3',2':4,5]furo[2,3-H]pyrano[3,4-c]chromene-1,12-dione #AF G2
Show more names
AFLATOXIN G2AFLATOXIN G2(RG)AFLATOXIN G2(RG) 10mgAflatoxinG2,crystallineAflatoxin G2Aflatoxin G2 0.5ug/ml in ACNAflatoxin G2 Solution, 3 Mg/LAflatoxin G2 solution

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
80.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
1
Heavy atoms
24
Formal charge
0
Complexity
626

Experimental & physicochemical properties

Melting Point237 - 240 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
237 · 237-240 °C
alpha
-473 ° · D -473° (c = 0.084 in chloroform)
Boiling point
387.74 °C · 387.74°C (rough estimate)
Density
1.3099 · 1.3099 (rough estimate)
refractive index
1.479 · 1.4790 (estimate)
Flash point
2 °C · 2 °C
storage temp.
2 · 2-8°C
solubility
DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
form
White to yellow powder. Blue-green fluorescence.
color
White to off-white
Water Solubility
15 mg/L · 15mg/L(temperature not stated)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Administration of phonobarbital enhances hepatic transformation activities and also protects against AFB-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. (A704, L1879)

Health Effects · 1 item

The main target organ in mammals is the liver so aflatoxicosis is primarily a hepatic disease. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Moreover, protracted exposure to aflatoxins has been associated with hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Thus, it is not clear in these various instances whether aflatoxin is a primary cause of the disease, is an innocent bystander which accumulates secondary to the disease process, or is a contributing cause in conjunction with other factors. It is also mutagenic and teratogenic. Inhaled aflatoxins may produce pulmonary adenomatosis. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. (A704, L1956)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. (L1877, A2859, A2972)

Chemistry & industry

Pharmacology

Metabolism/MetabolitesAflatoxins are metabolized in the liver by the cytochrome P-450-dependent polysubstrate mono-oxygenase system to less toxic metabolites. The main reactions in aflatoxin metabolism are hydroxylation, oxidation, and demethylation. (A2973)
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 1 item

The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Crops which are frequently affected include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). The toxin can also be found in the milk of animals which are fed contaminated feed. Thus, aflatoxins are usually encountered in thecontext of chronic exposure, via food intake or secondary to the handling of foodstuffs. (L1956)

Applications · 3 items

UsesAflatoxin G2 is the minor analogue of the green fluorescent family of bisfuranocoumarin mycotoxins produced by Aspergillus flavus and related species. Alfatoxins are one of the most potent mycotoxins known but are in fact "pre-toxins", requiring metabolic activation to the toxic principle. Aflatoxins are found widely in nature in trace amounts, particularly in grains and nuts. The toxicity of these metabolites was first recognised in the 1950s and their structures elucidated in 1963. Aflatoxins have been extensively reviewed.

UsesAflatoxins B1, B2, G1, G2 as secondary metabolites of fungal species such as Aspergillus flavus or Aspergillus parasiticus growing on a variety of foods (peanuts, nuts, spices, cereals). Aflatoxins are a group of very carcinogenic mycotoxins with hepatotoxic effects.

Very light and fluffy crystalline solid. Exhibits green-blue fluorescence.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
7241-98-7
PubChem CID
23670
BRN
1692017 · 1692017
Henry's Law Constant
9 · 9.0×108 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
cleaning productscosmeticsfood and beveragespersonal care
InChI
InChI=1S/C17H14O7/c1-20-9-6-10-12(8-3-5-22-17(8)23-10)14-11(9)7-2-4-21-15(18)13(7)16(19)24-14/h6,8,17H,2-5H2,1H3/t8-,17+/m0/s1
InChIKey
WPCVRWVBBXIRMA-WNWIJWBNSA-N
SMILES
C1(=O)OC2C3[C@]4([H])CCO[C@]4([H])OC=3C=C(OC)C=2C2CCOC(=O)C1=2
LogP
0.443 · 0.443 (est)
FDA UNII
2 MS0D8WA29 · 2MS0D8WA29
EPA Substance Registry System
2 · Aflatoxin G2 (7241-98-7)
UNSPSC Code
85151701 · 85151701
NACRES
77 · NA.77
Symbol(GHS)
2 · GHS02,GHS07,GHS08
Signal word
Danger
Hazard statements
225 · H225-H304-H315-H319-H340-H350-H372-H412
Precautionary statements
210 · P210-P273-P301+P310-P303+P361+P353-P305+P351+P338-P331
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
T+,T,Xn,F
Risk Statements
45 · 45-26/27/28-36-20/21/22-11-39/23/24/25-23/24/25-65-48/23/24/25-36/38-46
Safety Statements
53 · 53-28-36/37-45-36-26-16-7-62
RIDADR
3462 · UN 3462 6.1/PG 1
WGK Germany
3 · 3
RTECS
1700000 · LV1700000
HazardClass
6.1 · 6.1(a)
PackingGroup
I
HS Code
30029090 · 30029090
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Hazardous Substances Data
7241 · 7241-98-7(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in day old duckling: 172.5 mg/50 gm body wt (Carnaghan)
Signs and SymptomsA broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. (L1879)
Carcinogen Classification1, carcinogenic to humans (L135)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
rtecs
LV1700000
ridadr
UN 3462 6.1/PG 1
hs_code
30029090
Toxicity
LD50 orally in day old duckling: 172.5 mg/50 gm body wt (Carnaghan)
risk_code
45-26/27/28-36-20/21/22-11-39/23/24/25-23/24/25-65-48/23/24/25-36/38-46
Signal word
Danger
Symbol(GHS)
GHS02,GHS07,GHS08
hazard_code
T+,T,Xn,F
safety_code
53-28-36/37-45-36-26-16-7-62
hazard_class
6.1(a)
Storage Class
3 - Flammable liquids
packing_group
I
Hazard statements
H225-H304-H315-H319-H340-H350-H372-H412
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Precautionary statements
P210-P273-P301+P310-P303+P361+P353-P305+P351+P338-P331
Hazardous Substances Data
7241-98-7(Hazardous Substances Data)
General Description

Suppliers88 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
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青岛贞开生物医药技术有限公司0532-58268781 18561687109 · [email protected]
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Novachemistry44-20819178-90 02081917890 · [email protected]
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陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]

Additional notes

DefinitionChEBI: Aflatoxin G2 is a member of coumarins.