(S)-(+)-アブシジン酸

Abscisic Acid

HCID 5280896CAS 21293-29-8
部分構造検索類似構造を探す

基本情報

標準SMILES
CC1=CC(=O)CC(C)(C)[C@@]1(O)/C=C/C(C)=C\C(=O)O
InChIKey
JLIDBLDQVAYHNE-YKALOCIXSA-N
分子式
C15H20O4
平均分子量
264.32 g/mol
単同位体質量
264.13615912

概要

(+)-abscisic acid is the naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold. It has a role as a plant hormone and a plant metabolite. It is a conjugate acid of a (+)-abscisate. It is an enantiomer of a (-)-abscisic acid.

名称と識別子

優先名称
Abscisic Acid
IUPAC
(2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
現地名
(S)-(+)-アブシジン酸
英語名
(+)-Abscisic acid
分子式
C15H20O4
分子量
264.32

名称と別名

21293-29-8ABSCISIC ACIDAbscisin IIDormin72S9A8J5GWNSC-146877NSC-148832AbscissinsAbscissic Acid2,4-Pentadienoic acid, 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-, (S-(Z,E))-RefChem:914905(2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-1-cyclohex-2-enyl)-3-methylpenta-2,4-dienoic acid
名称をさらに表示
(S)-(+)-アブシジン酸(+)-アブシシンII(2Z,4E)-5-[1-ヒドロキシ-2,6,6-トリメチル-4-オキソ-2-シクロヘキセン-1β-イル]-3-メチル-2,4-ペンタジエン酸(+)-(cis,trans)-アブシシン酸(+)-cis-アブシシン酸(2Z,4E)-5-(1-ヒドロキシ-2,6,6-トリメチル-4-オキソ-2-シクロヘキセン-1β-イル)-3-メチル-2,4-ペンタジエン酸cis,trans-アブシシン酸(S)-(+)-アブシシン酸(2Z,4E)-3-メチル-5-(1α-ヒドロキシ-2,6,6-トリメチル-4-オキソ-2-シクロヘキセン-1-イル)-2,4-ペンタジエン酸cis-アブシシン酸(+)-アブシジン酸(+)-アブシシン酸ドルミン【器官脱離因子】(+)-(S)-アブシシン酸ドルミン(2Z,4E)-3-メチル-5-[(1S)-1α-ヒドロキシ-2,6,6-トリメチル-4-オキソ-2-シクロヘキセン-1-イル]-2,4-ペンタジエン酸2-cis-アブシシン酸[2Z,4E,(+)]-5-[(S)-1-ヒドロキシ-2,6,6-トリメチル-4-オキソ-2-シクロヘキセン-1-イル]-3-メチル-2,4-ペンタジエン酸アブシシンIIcis-trans-(+)-アブシシン酸S-ABAABK(S)-(+)-ABSCISIC ACID(+)-ABA(+)-abscisinii4-Bromo-5-chloroquinolineABA, ABKABSCISIN
(+-)-(CIS,TRANS)-ABSCISIC ACID244-319-5(2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid(+)-Abscisic acid(+)-cis,trans-Abscisic Acid(2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acidMFCD00066545ABA

データベース識別子

CAS
21293-29-8
PubChem CID
5280896
DTXSID
DTXSID0036766
ChEMBL
CHEMBL288040、CHEMBL379808
ChEBI
CHEBI:2365
UNII
72S9A8J5GW
EC Number
244-319-5
Nikkaji
J9.144H

物性

構造計算による物性

XLogP
1.6
極性表面積
74.6 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
3
重原子数
19

実験および物理化学的性質

Collision Cross Section · 2 件

174.4 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

173.8 Ų [M-H]-

物理化学的性質

融点
188 °C · 188 °C
比旋光度
20 · D20 +411.1° (c = 1 in ethanol); D20 +426.5° (c = 1 in 0.005N methanolic H2SO4)
沸点
327.55 °C · 327.55°C (rough estimate)
比重(密度)
1.0583 · 1.0583 (rough estimate)
屈折率
410 ° · 410 ° (C=0.2, EtOH)
貯蔵温度
2 · 2-8°C
化学的性質 · 1 件

化学的特性(+)-Abscisic acid (pure substance) is a colorless crystalline solid. It has a melting point of 160–161°C and sublimes at 120°C. The partition coefficients are 1.8 for the electrically neutral form and 0.94 for the ionic form. Its relative density is 1.21. The solubility in water is 3102 mg/L (at pH 4). The specific rotation is [α]²⁰D = +40.997° (c = 10.1 mg/mL in ethanol, at 20°C). The pKa is 4.61. It is soluble in chloroform, acetone, ethyl acetate, and diethyl ether but only sparingly soluble in benzene and water. The UV maximum absorption wavelength (in methanol) is 252 nm.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.4% (2 of 140) of reports.

Warning

H400 (97.9%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

危険有害性情報

Regulatory Information · 2 件

Commission Regulation (EU) No 188/2011

Abscisic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and Categories · 2 件

Aquatic Acute 1 (97.9%)

Aquatic Acute 1

安全データ

F
8
wgk
3
rtecs
RZ2475100
hs_code
29189900
safety_code
22-24/25
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1

化学と産業

薬理情報

MeSH Pharmacological Classification · 6 件

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Drugs used to prevent NAUSEA or VOMITING.

Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

応用分野 · 3 件

解説アブシジン酸，高等植物に広く存在する植物ホルモンの一種。成長を抑制する作用をもち，落葉や休眠，養分の蓄積を促進する。また，種子や冬芽の発芽を抑制する。気孔を閉じさせる作用もある。

用途アブシシン酸（アブシシンさん、アブシジン酸、英: abscisic acid、ABA）は、植物ホルモンの一種。構造的にはセスキテルペンに属する。休眠や生長抑制、気孔の閉鎖などを誘導する。また乾燥などのストレスに対応して合成されることから「ストレスホルモン」とも呼ばれる。

使用(+)-Abscisic acid is the natural isomer of the abscission-accelerating plant hormone and a plant growth regulator that exhibits multiple physiological effects, including inducing plant dormancy, inhibiting seed germination and plant growth, and stimulating stomatal closure.

調製方法 · 2 件

合成方法(JOC, 1989, 54, 681)

純化方法Crystallise the acid from CCl4/pet ether, EtOH/hexane and sublime it at 120o. Also purify it by dissolving ~30g in 30mL of EtOAc, adding 100mL of hexane and allow to crystallise overnight (yield 8.4g), m 156-158o, 161-163o, [] D +426o (c 0.005M H2SO4 in MeOH). [Cornforth et al. Nature (London) 206 715 1965, Soukemp et al. Helv Chim Acta 72 361 1989.] The RS-isomer was purified on a Kieselgel F254 plate with toluene/EtOAc/AcOH (50:50:3) and has m 188-190o [Cornforth et al. Aust J Chem 45 179 1992]. [Beilstein 17/3 V 13.]

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補足説明

定義ChEBI: The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.

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