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6′,-7′-ジヒドロキシベルガモチン

6',7'-Dihydroxybergamottin

HCID 6440498
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基本情報

CAS
145414-76-2
標準SMILES
C/C(=C\COc1c2ccoc2cc2oc(=O)ccc12)CCC(O)C(C)(C)O
InChIKey
IXZUPBUEKFXTSD-MDWZMJQESA-N
分子式
C21H24O6
平均分子量
372.4 g/mol
単同位体質量
372.15728848

概要

6',7'-Dihydroxybergamottin is a member of psoralens.

名称と識別子

優先名称
6',7'-Dihydroxybergamottin
IUPAC
4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
現地名
6′,-7′-ジヒドロキシベルガモチン
英語名
6',7'-Dihydroxybergamottin
分子式
C21H24O6
分子量
372.41

名称と別名

145414-76-26',7'-dihydroxybergamottin6,7-dihydroxybergamottin6,7-DHBDTXSID0010454014-[(E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-oneRefChem:9136244-((E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy)furo(3,2-g)chromen-7-oneDTXCID0015273365-(((2E)-6-hydroxy-3,7,7-trimethyloct-2-en-1-yl)oxy)-2H,8H-pyrano(3,2-g)chromen-2-one6',7'-dihydroxy Bergamottin71339-34-9
名称をさらに表示
6′,-7′-ジヒドロキシベルガモチン4-[[(E)-6,7-ジヒドロキシ-3,7-ジメチル-2-オクテニル]オキシ]-7H-フロ[3,2-g][1]ベンゾピラン-7-オン4-[(E)-3,7-ジメチル-6,7-ジヒドロキシ-2-オクテン-1-イルオキシ]-7H-フロ[3,2-g][1]ベンゾピラン-7-オン4-{[(2E)-6,7-ジヒドロキシ-3,7-ジメチルオクタ-2-エン-1-イル]オキシ}-7H-フロ[3,2-g]クロメン-7-オン4-[[(2E)-3,7-ジメチル-6,7-ジヒドロキシ-2-オクテニル]オキシ]-7H-フロ[3,2-g][1]ベンゾピラン-7-オン4-[[(E)-3,7-ジメチル-6,7-ジヒドロキシ-2-オクテニル]オキシ]-7H-フロ[3,2-g][1]ベンゾピラン-7-オン4-[[(2E)-3,7-ジメチル-6,7-ジヒドロキシ-2-オクテン-1-イル]オキシ]-7H-フロ[3,2-g][1]ベンゾピラン-7-オン6′,7′-ジヒドロキシベルガモッチン6,7-dihydroxybergaMottin(DHB)
6,7-Dihydroxy bergamottin4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-(E)-4-((6,7-Dihydroxy-3,7-dimethyloct-2-en-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl)oxy]-4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-oneCHEMBL513494SCHEMBL30173389

データベース識別子

CAS
145414-76-2、71339-34-9
PubChem CID
6440498
DTXSID
DTXSID001045401
ChEMBL
CHEMBL513494
ChEBI
CHEBI:175789
Nikkaji
J687.532G、J784.174D

物性

構造計算による物性

XLogP
3.4
極性表面積
89.1 Ų
水素結合供与体数
2
水素結合受容体数
6
回転可能結合数
7
重原子数
27
形式電荷
0
複雑度
595

物理化学的性質

融点
112 · 112-113 °C
沸点
578.2 · 578.2±50.0 °C(Predicted)
比重(密度)
1.26 · 1.260
貯蔵温度
2 · 2-8°C
溶解性
エタノール:可溶
酸解離定数(Pka)
14.65 · 14.65±0.29(Predicted)
外見
個体
色
ホワイトからオフホワイト
InChI
1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+
InChIKey
IXZUPBUEKFXTSD-MDWZMJQESA-N
SMILES
C\C(CCC(O)C(C)(C)O)=C/COc1c2C=CC(=O)Oc2cc3occc13

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Health Effects · 1 件

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 件

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). 6,7-Dihydroxybergamottin also acts as a CYP3A4 inhibitor (A3109).

Carcinogen Classification · 1 件

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)

安全データ

wgk
3
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological ClassificationDrugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES.
応用分野 · 2 件

説明6,7-dihydroxy Bergamottin (6,7-DHB) is a potent inhibitor of CYP3A4 (IC50 = 25 μM). It appears to be the primary compound in grapefruit juice that is responsible for inhibition of testosterone 6β-hydrolase activity. Ingestion of grapefruit juice during treatment regimes with drugs normally metabolized by cytochrome P450 enzymes of the CYP3A subfamily results in a substantial increase in plasma concentration of these agents. However, giving a patient grapefruit juice or just 6,7-DHB could be advantageous in cases where a drug is metabolized too quickly by CYP3A4.

使用A minor metabolite of Bergamottin. Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5.

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