Record Information
Version1.0
Creation date2010-04-08 22:09:14 UTC
Update date2018-05-29 00:50:49 UTC
Primary IDFDB010669
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Naphthaleneacetic acid
DescriptionPlant growth regulator. It is used for control of preharvest fruit drop, flower induction and fruit thinning in various crops such as apples, potatoes, olives and citrus fruits 1-Naphthaleneacetic acid (NAA) is a plant hormone in the auxin family. It is a rooting agent and used for the vegetative propagation of plants from stem and leaf cutting. It is also used for plant tissue culture. NAA does not occur naturally. Under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides.
CAS Number86-87-3
Structure
Thumb
Synonyms
SynonymSource
alpha-NAAChEBI
alpha-Naphthaleneacetic acidChEBI
NAAChEBI
NAPHTHALEN-1-yl-acetIC ACIDChEBI
Naphthalene-1-acetic acidChEBI
alpha-Naphthylacetic acidKegg
a-NAAGenerator
Α-naaGenerator
a-NaphthaleneacetateGenerator
a-Naphthaleneacetic acidGenerator
alpha-NaphthaleneacetateGenerator
Α-naphthaleneacetateGenerator
Α-naphthaleneacetic acidGenerator
NAPHTHALEN-1-yl-acetateGenerator
Naphthalene-1-acetateGenerator
a-NaphthylacetateGenerator
a-Naphthylacetic acidGenerator
alpha-NaphthylacetateGenerator
Α-naphthylacetateGenerator
Α-naphthylacetic acidGenerator
1-NaphthaleneacetateGenerator
(1-Naphthyl)acetic acid, bsi, isoHMDB
1-NAAHMDB
1-Naphthylacetic acidHMDB
2-(alpha-Naphthyl)ethanoic acidHMDB
Fruitone NHMDB
PhyomoneHMDB
PlanofixHMDB
Tre-holdHMDB
1-Naphthaleneacetic acid, ammonium saltHMDB
1-Naphthaleneacetic acid, potassium saltHMDB
1-Naphthaleneacetic acid, sodium saltHMDB
Galle-donauHMDB
2-(1-Naphthyl)acetic acidMeSH
Sodium 1-naphthaleneacetateMeSH
Potassium 1-naphthaleneacetateMeSH
2-(Naphthalen-1-yl)acetic acidMeSH
1-Naphthaleneacetic acidChEBI
1-NaphthylacetateGenerator
(1-Naphthyl)acetic acid, BSI, ISOdb_source
Tre-Holddb_source
α-naaGenerator
α-naphthaleneacetateGenerator
α-naphthaleneacetic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.82 m³·mol⁻¹ChemAxon
Polarizability19.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H10O2
IUPAC name2-(naphthalen-1-yl)acetic acid
InChI IdentifierInChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
InChI KeyPRPINYUDVPFIRX-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=C2C=CC=CC2=CC=C1
Average Molecular Weight186.2066
Monoisotopic Molecular Weight186.068079564
Classification
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.40%; H 5.41%; O 17.18%DFC
Melting PointMp 134.5-135.5° (131°)DFC
Boiling PointNot Available
Experimental Water Solubility0.42 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.24SANGSTER (1993)
Experimental pKapKa 4.24 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae35View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-217de62c6bdb645dae35View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-782f3a027c45e64394b3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-b2d7fccbd30cb458042cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-61aa1017aa8bebaf379aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-7120093ba4bbf767a44cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-6cb2846bdf5a8ff0ae2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-1900000000-e7c306f143bdff24d139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0900000000-d15319af97ab9db3a9feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0900000000-789eede2b113302cededView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-0900000000-d12c6543cee99c510a52View in MoNA
ChemSpider ID6601
ChEMBL IDCHEMBL428495
KEGG Compound IDC13014
Pubchem Compound ID6862
Pubchem Substance IDNot Available
ChEBI ID32918
Phenol-Explorer IDNot Available
DrugBank IDDB01750
HMDB IDHMDB32708
CRC / DFC (Dictionary of Food Compounds) IDFMC74-P:FMC74-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNLA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID1-Naphthaleneacetic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference