基本情報
- CAS
1143-38-0- 標準SMILES
O=C1c2c(O)cccc2Cc2cccc(O)c21- InChIKey
NUZWLKWWNNJHPT-UHFFFAOYSA-N- 分子式
- C14H10O3
- 平均分子量
- 226.23 g/mol
- 単同位体質量
- 226.06299418
名称と識別子
- 優先名称
- Anthralin
- IUPAC
- 1,8-dihydroxy-10H-anthracen-9-one
- 現地名
- 1,8-ジヒドロキシアントロン
- 英語名
- ANTHRALIN
- 分子式
- C14H10O3
- 分子量
- 226.23
名称と別名
名称をさらに表示
データベース識別子
- CAS
1143-38-0- PubChem CID
- 2202
- DTXSID
DTXSID7024538- ChEMBL
CHEMBL46469- ChEBI
CHEBI:37510- UNII
- U8CJK0JH5M
- EC Number
- 214-538-0
- Nikkaji
- J5.224H
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 57.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 287
実験および物理化学的性質
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
not soluble in water
Melting Point
349 to 358 °F (NTP, 1992)
178-182 °C
Collision Cross Section
142.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
142.24 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];142.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];151.92 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 178 · 178-181 °C (lit.)
- 沸点
- 464.1 · 464.1±45.0 °C(Predicted)
- 比重(密度)
- 1.419 · 1.419±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 水にほとんど溶けず、ジクロロメタンに溶け、アセトンに溶けにくく、エタノールに溶けにくい (96%)。アルカリ金属水酸化物の希薄溶液に溶けます。
- 外見
- Solid
- 酸解離定数(Pka)
- 7.16 · 7.16±0.20(Predicted)
- 色
- イエローからオレンジ、ダークイエロー
- 水溶解度
- 20 mg/mL)、アセトン、ベンゼン、アルカリ金属水酸化物溶液、固定油に可溶。 · 水に溶けません。酢酸、クロロホルム(20mg/mL)、アセトン、ベンゼン、アルカリ金属水酸化物溶液、固定油に可溶。 95% エタノール、アルコール、エーテル、氷酢酸にわずかに溶けます。
- Merck
- 14 · 14,684
- BRN
- 2054360 · 2054360
- 安定性
- 安定。可燃性。強力な酸化剤とは相容れない。
- InChI
- 1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2
- InChIKey
- NUZWLKWWNNJHPT-UHFFFAOYSA-N
- SMILES
- Oc1cccc2Cc3cccc(O)c3C(=O)c12
- CAS データベース
- 1143 · 1143-38-0(CAS DataBase Reference)
- EPAの化学物質情報
- Dithranol (1143-38-0)
化学的性質
化学的特性Yellow Crystalline Solid
安全と法規制
GHS分類
GHS Classification
Warning
H315 (98.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (98.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (96.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
Regulatory Information
Chemical: 9(10H)-Anthracenone,1,8-dihydroxy-
Anthralin: Does not have an individual approval but may be used under an appropriate group standard
安全と保護具
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should protect this material from light and moisture, and store it in a refrigerator. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
毒性情報
Carcinogen Classification
Dithranol
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 13: (1977) Some Miscellaneous Pharmaceutical Substances;Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)
1987
1987
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Topical anthralin has not been studied during breastfeeding. Anthralin has suspected mutagenic properties, so it should only be used if the potential benefit to the mother justifies potential risk to the infant. If anthralin is used, ensure that the infant's skin does not come into direct contact with the areas of maternal skin that have been treated and the infant does not ingest the product from the mother's skin.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
法規制情報
Regulatory Information
Chemical: 9(10H)-Anthracenone,1,8-dihydroxy-
Anthralin: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- wgk
- 3
- rtecs
- CB8927000
- hs_code
- 29144000
- risk_code
- 36/37/38-45
- hazard_code
- Xi,T
- safety_code
- 26-53-45
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
D - Dermatologicals;D05 - Antipsoriatics;D05A - Antipsoriatics for topical use;D05AC - Antracen derivatives;D05AC01 - Dithranol
QD - Dermatologicals;QD05 - Drugs for keratoseborrheic disorders (atc human: antipsoriatics);QD05A - Drugs for keratoseborrheic disorders, topical use (atc human: antipsoriatics for topical use);QD05AC - Antracen derivatives;QD05AC01 - Dithranol
Pharmacodynamics
Anthralin is a natural anthraquinone derivative, anti-psoriatic and anti-inflammatory agent. It controls skin growth by reducing the synthesis of DNA and the mitotic activity in the hyperplastic epidermis, normalizing the rate of cell proliferation and keratinization.
Mechanism of Action
Anthralin inhibits the proliferation of keratinocytes (epidermal skin cells), prevents the action of T-cells, and promotes cell differentiation, likely through mitochondrial dysfunction. In addition, the production of free radicals may contribute to its anti-psoriatic effect. In vitro studies demonstrate that anthralin prolongs the prophase component of mitosis for keratinocytes and leukocytes. Prophase is the first step of mitosis, the process separating the duplicated genetic material carried in the nucleus of a parent cell into two identical daughter cells. In vivo studies demonstrate that anthralin blocks DNA synthesis and can increase the release of reactive oxygen species. Anthralin is believed to normalize the rate of epidermal cell proliferation and keratinization by reducing the mitotic activity of the epidermal hyperplasia in psoriasis. Anti-proliferative and anti-inflammatory effects of anthralin have been demonstrated on both psoriatic and healthy skin. The anti-proliferative effects of anthralin are thought to be due to a combination of inhibition of DNA synthesis and its strong reducing properties. The effectiveness of anthralin as an anti-psoriatic agent is partly owed to its ability to promote lipid peroxidation and reduce the concentration of endothelial adhesion molecules, which are found to be elevated in psoriatic patients,. Recent studies suggest that its ability to prevent T-lymphocyte activation and normalize keratinocyte differentiation may occur by a direct effect on mitochondria.
Metabolism/Metabolites
Anthralin is administered topically. Although the extent of systemic absorption after topical application has not been determined, no traces of anthraquinone metabolites were detected in the urine of treated subjects in a limited clinical study of anthralin cream,. Anthralin does not inhibit hepatic microsomal enzyme activity.
用途と製造
Uses
Synthetic Polymer MALDI Matrix Compounds
Use (kg; approx.) in Germany (2009): >10;Consumption (g per capita; approx.) in Germany (2009): 0.000122;Calculated removal (%): 80.4
応用分野
説明Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation. It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM. Anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17A- and IL-22-stimulated NHKs. It also inhibits leukotriene B4 (LTB4; ) production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC50 = 7 μM). Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.
使用Antipsoriatic
一般的な説明Lemon yellow leaflets or plates or an orange powder. Melting point 176-181°C. No odor or taste. Insoluble in water. Moderately toxic by ingestion, inhalation and skin absorption. Used as a treatment for psoriasis.
上流・下流製品情報
下流製品
サプライヤー100 社
補足説明
定義ChEBI: An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.
関連反応
化合物ノート
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