化工社化工社 化学情報印刷レポート · 研究参考用
1,8-ジヒドロキシアントロン
アントラリン · シグノリン · ジトラノール · 1,8-ジヒドロキシアントラセン-9(10H)-オン · 1,8-ジヒドロキシ-9(10H)-アントラセノン · 1,8-ジヒドロキシアントロン · ジスラノール · 1,8-ジヒドロキシ-9,10-ジヒドロアントラセン-9-オン
識別子と物理属性
| CAS No. | 1143-38-0 |
|---|---|
| 分子式 | C14H10O3 |
| 平均分子量 | 226.23 g/mol |
| 単同位体質量 | 226.06299418 g/mol |
| SMILES | O=C1c2c(O)cccc2Cc2cccc(O)c21 |
| InChIKey | NUZWLKWWNNJHPT-UHFFFAOYSA-N |
| PubChem CID | 2202 |
| ChEMBL | CHEMBL46469 |
| ChEBI | CHEBI:37510 |
| EC No. | 214-538-0 |
| DTXSID | DTXSID7024538 |
| 現地名 | 1,8-ジヒドロキシアントロン |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 57.5 |
| 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 |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)not soluble in water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。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。 |
| 融点 | 349 to 358 °F (NTP, 1992)178-182 °C178-181 °C (lit.) |
| Physical Description | 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. |
| Kovats Retention Index | 2220 |
| Collision Cross Section | 142.6 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]142.24 Ų [M+H-H2O]+ [CCS Type: TW142.86 Ų [M+H]+ [CCS Type: TW151.92 Ų [M+Na]+ [CCS Type: TW |
| 沸点 | 464.1±45.0 °C(Predicted) |
| 密度 | 1.419±0.06 g/cm3(Predicted) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | Solid |
| pKa（酸解離定数） | 7.16±0.20(Predicted) |
| 色 | イエローからオレンジ、ダークイエロー |
| Merck | 14,684 |
| BRN | 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 | 1143-38-0(CAS DataBase Reference) |
| EPAの化学物質情報 | Dithranol (1143-38-0) |
化学的特性
Yellow Crystalline Solid
安全性と法規制
| GHS 分類 | WarningH315 (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 exposureRespiratory 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. |
|---|---|
| 規制情報 | Chemical: 9(10H)-Anthracenone,1,8-dihydroxy-Anthralin: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - 9(10H)-Anthracenone,1,8-dihydroxy-: Environment tier I assessmentIMAP assessments - 9(10H)-Anthracenone,1,8-dihydroxy-: Human health tier I assessment |
| 火災危険 | Flash point data are not available for this chemicalhowever, it is probably combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: This compound may cause irritation, lacrimation and photophobia.ACUTE/CHRONIC HAZARDS: This compound may cause irritation. It may also cause lacrimation. (NTP, 1992) |
| 反応性グループ | KetonesPhenols and Cresols |
| Reactivity Profile | ANTHRALIN reacts as a weak acid. Soluble in aqueous bases. May react with strong oxidizing agents. May be sensitive to light and moisture (NTP, 1992). |
| Air and Water Reactions | Unstable in air when in alkaline solution. Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (98.3%)Eye Irrit. 2 (98.3%)STOT SE 3 (96.7%) |
| 消火 | Fires involving this compound should be controlled usin a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 応急処置 | 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 areatake 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 usedif 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) |
| 非火災時の漏出対応 | 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) |
| Carcinogen Classification | DithranolGroup 3: Not classifiable as to its carcinogenicity to humansVolume 13: (1977) Some Miscellaneous Pharmaceutical SubstancesVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print) |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during LactationTopical 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 InfantsRelevant published information was not found as of the revision date.◉ Effects on Lactation and Breastmilk |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | CB8927000 |
| 税関コード | 29144000 |
| 危険文句（R） | 36/37/38-45 |
| 危険表示 | Xi,T |
| 安全措置（S） | 26-53-45 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.