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Isobergapten

HCID 68082
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
482-48-4
Standard SMILES
COc1cc2occc2c2oc(=O)ccc12
InChIKey
AJSPSRWWZBBIOR-UHFFFAOYSA-N
Molecular formula
C12H8O4
Average molar mass
216.19 g/mol
Monoisotopic mass
216.04225873

Overview

Isobergapten is a furanocoumarin.

Names & identifiers

Preferred name
Isobergapten
IUPAC
5-methoxyfuro[2,3-h]chromen-2-one
English name
ISOBERGAPTEN
Molecular formula
C12H8O4
Molecular weight
216.19

Names & synonyms

IsobergaptenIsobergaptene5-Methoxy-2H-furo[2,3-H]chromen-2-one5-MethoxyangelicinISO-BERGAPTENUNII-27X3V737WH2H-Furo[2,3-h]-1-benzopyran-2-one, 5-methoxy-27X3V737WH5-Methoxy-2H-furo(2,3-h)-1-benzopyran-2-one2H-Furo(2,3-h)-1-benzopyran-2-one, 5-methoxy-DTXSID80754155-BENZOFURANACRYLIC ACID, 4-HYDROXY-6-METHOXY-, .DELTA.-LACTONE
Show more names
AKOS 244-72IsobergatenIsobergapten-RMISOBERGATEN WITH HPLCISOBERGAPTEN(AS) 10mgISOBERGAPTEN WITH HPLCISOBERGAPTEN (Standard)
5-Methoxy-2H-furo(2,3-H)chromen-2-oneRefChem:149045DTXCID60406125-BENZOFURANACRYLIC ACID, 4-HYDROXY-6-METHOXY-, DELTA-LACTONEAJSPSRWWZBBIOR-UHFFFAOYSA-N482-48-45-methoxyfuro[2,3-h]chromen-2-oneMFCD00016756

Database identifiers

CAS
482-48-4
PubChem CID

Properties

Computed structural properties

XLogP
2
Topological polar surface area
48.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
16
Formal charge
0
Complexity
325

Experimental & physicochemical properties

Collision Cross Section · 2 items

137.88 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

139.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
222 °C · 222°C
Boiling point
412.4 · 412.4±45.0 °C(Predicted)
Density
1.368 · 1.368
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly, Heated)
form
Solid
color
White to Off-White
Water Solubility
insoluble in water
InChI
1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3
InChIKey
AJSPSRWWZBBIOR-UHFFFAOYSA-N
SMILES
[o]1c2c(c3c(c(c2)OC)C=CC(=O)O3)cc1

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Sens. 1 (100%)

Toxicology

Health Effects · 1 item

The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.

Toxicity Summary · 1 item

Inhibits insect cytochrome P450 (L579). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (L579).

Chemistry & industry

Applications

Usesantifungal,

Upstream & downstream products

Upstream raw materials

BERGAPTOLDimethyl sulfate

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
河南赢创生物科技有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
68082
DTXSID
DTXSID8075415
ChEMBL
CHEMBL141690
ChEBI
CHEBI:81487
UNII
27X3V737WH
EC Number
683-112-8
Nikkaji
J13.193H
LogP
2.34 · 2.340 (est)
FDA UNII
27 X3V737WH · 27X3V737WH
EPA Substance Registry System
2 H-Furo[2,3-h]-1-benzopyran-2-one, · 2H-Furo[2,3-h]-1-benzopyran-2-one, 5-methoxy- (482-48-4)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317
Precautionary statements
261 · P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
WGK Germany
3 · WGK 3
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 · Skin Sens. 1
Signs and SymptomsFurocoumarin toxins can cause stomach ache and may also cause a painful skin reaction when contact with the parsnip plant is combined with UV rays from sunlight. (L579)
Carcinogen Classification · 1 item

Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135)

Safety data

wgk
WGK 3
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H317
Hazard Classifications
Skin Sens. 1
Precautionary statements
P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
16650615803 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
湖北丹鼎医药科技有限公司18917019315(微信同号) 17701422019 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
武汉市皇臻生物化工有限公司13795480948 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
成都麦德生科技有限公司028-82253651 18140204969 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
ALB Technology Limited702-983-3769 · [email protected]
成都钠钶锂生物科技有限公司028-61983833 19138982515 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
四川精萃天成药物科技有限公司028-87865381 18108190480 · [email protected]
上海萄普生物医药技术有限公司15900573766 18018507602 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: Isobergapten is a furanocoumarin.