Basic information
- CAS
21293-29-8- Standard SMILES
CC1=CC(=O)CC(C)(C)[C@@]1(O)/C=C/C(C)=C\C(=O)O- InChIKey
JLIDBLDQVAYHNE-YKALOCIXSA-N- Molecular formula
- C15H20O4
- Average molar mass
- 264.32 g/mol
- Monoisotopic mass
- 264.13615912
Overview
(+)-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.
Names & identifiers
- Preferred name
- 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
- English name
- (+)-Abscisic acid
- Molecular formula
- C15H20O4
- Molecular weight
- 264.32
Names & synonyms
Show more names
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 494
Experimental & physicochemical properties
Collision Cross Section
174.4 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
173.8 Ų [M-H]-
Physicochemical properties
- Melting point
- 188 °C · 188 °C
- alpha
- 20 · D20 +411.1° (c = 1 in ethanol); D20 +426.5° (c = 1 in 0.005N methanolic H2SO4)
- Boiling point
- 327.55 °C · 327.55°C (rough estimate)
- Density
- 1.0583 · 1.0583 (rough estimate)
- refractive index
- 410 ° · 410 ° (C=0.2, EtOH)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethanol (Sparingly), Methanol (Slightly)
- form
- Off-white powder
- pka
- 4.87 · 4.87±0.33(Predicted)
- color
- White to Pale Yellow
- optical activity
- 415 · [α]/D 415±10°, c = 0.1 in ethanol
- Merck
- 14 · 14,11
- BRN
- 2698956 · 2698956
- Stability
- Light Sensitive
- InChI
- 1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m1/s1
- InChIKey
- JLIDBLDQVAYHNE-WEYXYWBQSA-N
- SMILES
- CC(\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O
- LogP
- 1.896 · 1.896 (est)
- CAS DataBase Reference
- 21293 · 21293-29-8(CAS DataBase Reference)
- FDA UNII
- 72 S9A8J5GW · 72S9A8J5GW
- EPA Substance Registry System
- 2 · 2,4-Pentadienoic acid, 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-, (2Z,4E)- (21293-29-8)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P271-P280
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 2475100 · RZ2475100
- F
- 8 · 8
- HS Code
- 29189900 · 29189900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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]
Hazard information
Regulatory Information
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
Aquatic Acute 1 (97.9%)
Aquatic Acute 1
Safety data
- F
- 8
- wgk
- 3
- rtecs
- RZ2475100
- hs_code
- 29189900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Applications
Uses(+)-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.
Suppliers100 total
Additional notes
DefinitionChEBI: 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.
Related reactions
Compound notes
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