基本情報
- CAS
481-06-1- 標準SMILES
CC1=C2[C@H]3OC(=O)[C@@H](C)[C@@H]3CC[C@@]2(C)C=CC1=O- InChIKey
XJHDMGJURBVLLE-BOCCBSBMSA-N- 分子式
- C15H18O3
- 平均分子量
- 246.3 g/mol
- 単同位体質量
- 246.12559443
概要
Alpha-santonin is a santonin that is 3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione substituted by methyl groups at positions 3, 5a and 9. It has a role as a plant metabolite. It is a santonin and a botanical anti-fungal agent.
名称と識別子
- 優先名称
- (-)-Santonin
- IUPAC
- (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
- 現地名
- サントニン
- 英語名
- Santonin
- 分子式
- C15H18O3
- 分子量
- 246.3
名称と別名
santoninalpha-Santonin481-06-1Semenen(-)-SantoninSantoninumSantoninic anhydrideL-alpha-SantoninDTXSID7045312NSC-49001VL8J38ERO(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
名称をさらに表示
サントニン(-)-サントニン(3S,3aS,5aS,9bS)-3a,5,5a,9b-テトラヒドロ-3,5a,9-トリメチルナフト[1,2-b]フラン-2,8(3H,4H)-ジオン(αS,1S)-α,4aα,8-トリメチル-1β-ヒドロキシ-7-オキソ-1,2,3,4,4a,7-ヘキサヒドロナフタレン-2α-酢酸ラクトンサントン酸無水物(3S)-3aβ,5,5a,9bα-テトラヒドロ-3β,5aα,9-トリメチルナフト[1,2-b]フラン-2,8(3H,4H)-ジオン(3S)-3,3aβ,4,5,5a,9bα-ヘキサヒドロ-3β,5aα,9-トリメチルナフト[1,2-b]フラン-2,8-ジオンα-サントニン(3S)-3β,5aα,9-トリメチル-2,3,3aβ,4,5,5a,8,9bα-オクタヒドロナフト[1,2-b]フラン-2,8-ジオン(3aS)-3a,5,5a,9bα-テトラヒドロ-3β,5aα,9-トリメチルナフト[1,2-b]フラン-2,8(3H,4H)-ジオン(3S)-3β,5aα,9-トリメチル-3aβ,4,5,9bα-テトラヒドロナフト[1,2-b]フラン-2,8(3H,5aH)-ジオンΑ‐サントニンサントニン, A-サントニン (JP17)(3S,3aS,5aS,9bS)-3,5a,9-トリメチル-2H,3H,3aH,4H,5H,5aH,8H,9bH-ナフト[1,2-b]フラン-2,8-ジオン
物性
構造計算による物性
- XLogP
- 2.3
- 極性表面積
- 43.4 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 500
実験および物理化学的性質
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
Collision Cross Section
154.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
154.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 172 · 172-173 °C(lit.)
- 沸点
- 329.3 °C · 329.3°C (rough estimate)
- 比重(密度)
- 1.59 · 1.5900
- 屈折率
- -172.5 ° · -172.5 ° (C=2, CHCl3)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- クロロホルム（わずかに）
- 外見
- Solid
- 色
- ホワイトからオフホワイト
- 水溶解度
- 0.2 g/L · 0.2g/L(17.5℃)
- Merck
- 14 · 14,8361
- BRN
- 89489 · 89489
- 安定性
- Hygroscopic
- InChI
- 1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1
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。
GHS分類
GHS Classification
Danger
H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (98.6%)
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LE3150000
- ridadr
- 2811
- hs_code
- 2932.99.7000
- risk_code
- 22-36/37/38-26/27/28
- hazard_code
- Xn,Xi,T+
- safety_code
- 22-24/25-45-37-36-28-26
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
MeSH Pharmacological ClassificationSubstances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
用途と製造
General Manufacturing InformationNaphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-: INACTIVE
応用分野
解説サントニン．セスキテルペンの一種．キク科Artemisia cinaのつぼみなどに1～4％ 含まれているが，わが国ではミブヨモギA.maritimaから単離している．回虫の頭部神経にはたらくけいれん毒で，駆虫薬として用いられる．α-サントニンは，融点171～172 ℃．[α]D－173°(エタノール)．11位の異性体であるβ-サントニンは，融点216～218 ℃．[α]D－137.2°(クロロホルム)．LD50 900 mg/kg(マウス，経口)．
説明Santonin is a lactone compound extracted from the flower bud of Artemisia cina Berg in Compositae, crown daisy chrysanthemum or other plants in Artemisia. It has been recorded in ancient China . Its English name is santonica wormseed, Chinese alias is ‘quhaosu’ and Latin name is Seriphidium cinum (Berg ex Poljak.) Pol-jak. . Santonica wormseed, a variant name for Artemisia cina Berg, is the leaf and anthotaxy of Artemisia cina Berg in sagebrush plants in Compositae. There are more than 100 plus in sagebrush, in which about 30 plus live in China, and parts of them can be used medicinally.Santonica wormseed, used as raw material to extract and manufacture santonin, lives in cold, dry sandy loam. The place of origin is the Southern Central Asia in the former Soviet Union. China introduced the earliest cultivation in Xinjiang, and now it is introduced and cultivated in the North, Northeast and Northwest China. Santonica wormseed mainly contains hispidulin, quercetin and caffeic acid, and its flower contains 1–3.5% α-santonin, 1–3% artemisinin and volatile oil (mainly is 1, 8-cineole) and so on. Leaf also contains a small amount of α-santonin. In addition, it also contains β-cintonin, 3,4,5,7-tetrahydroxy-3-methoxyflavone7- glucoside and aglucone.
来歴The study on the chemical properties and structure of santonin was carried out at the end of the nineteenth century all the earliest research works were from the Italian scholars, such as Cannizzaro, Andreocci, Gucci, Francesconi, etc. The chemical structures determined before 1910 were all not exactly correct. Until 1929–1930, British scholars, Clemo, Haworth and Walton, finally determined the exact structure of santonin for the transformation from synthesized santonin into desmotroposanto nin and santonous acid. However, until 1940, there were no reports on structural configuration. Chinese scholars, Huang Minglong et al., basically completed the research work on the structural configuration of santonin in 1951, and the results were proved by Japanese scholars, Abe, Y. and Harukawa et al. in 1954.
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