allenolic acid
6-hydroxy-2-naphthalenepropanoic acid
Identification
| Name | allenolic acid |
| CAS Number | 553-39-9 |
| FDA UNII | I2MQT1CC3H |
| Molecular Formula | C13 H12 O3 |
| Molecular Weight | 216.23624000 |
| Nikkaji Number | J11.552E |
| XlogP3 | 2.60 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 94.00 °C. @ 760.00 mm Hg |
| Boiling Point | 448.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 462.00 °F. TCC ( 238.90 °C. ) (est) |
| logP (o/w) | 2.330 (est) |
| Soluble in | water, 967.2 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for allenolic acid usage levels up to | not for fragrance use. |
| Recommendation for allenolic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
amphihydroxynaphthyl-b-propionic acid
6-
hydroxy-2-naphthalene propanoic acid
6-
hydroxy-2-naphthalenepropanoic acid
3-(6-
hydroxynaphthalen-2-yl)propanoic acid
2-
naphthalenepropanoic acid, 6-hydroxy-
PubMed:
Organophosphine-Catalyzed [4C+X] Annulations
PubMed:
[Allenolic acid and its derivatives]
PubMed:
Microbial transformation of artificial estrogens of the allenolic group
PubMed:
[Synthetic estrogens derived from allenolic acid]
PubMed:
Transcriptional regulation of estrogen-responsive genes by non-steroidal estrogens: doisynolic and allenolic acids
PubMed:
[Comparative effects of dimethyl-ethyl-allenolic acid and of estradiol on gestation in the mouse]
PubMed:
A synthesis of (-)-mintlactone
PubMed:
[Anesthetic effect of certain derivatives of allenolic acid]
PubMed:
[Comparison of the effects of estradiol and dimethyl-ethyl-allenolic acid]
PubMed:
[Production of mammary tumors by an allenolic acid derivative in male mice]
PubMed:
[About a new synthetic estrogen; du-methyl-ethyl-allenolic acid]
PubMed:
Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril
PubMed:
Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation
PubMed:
Enantioselective pathway for the synthesis of laurenditerpenol
PubMed:
Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with à-Methylallenoates
PubMed:
Organocatalysis for new chiral fullerene-based materials
PubMed:
[The antibacterial action of certain acids substituted in the alpha position with two methyl groups (allenolic acids and its analogs)]
PubMed:
Enantioselective Synthesis of a Furan Lignan (+)-Sylvone
PubMed:
Organocatalytic synthesis of highly functionalized pyridines at room temperature
PubMed:
Gold-catalyzed cascade cyclization-oxidative alkynylation of allenoates
PubMed:
A computational study of the activation of allenoates by Lewis bases and the reactivity of intermediate adducts
PubMed:
Phosphine-Catalyzed Doubly Stereoconvergent ?-Additions of Racemic Heterocycles to Racemic Allenoates: The Catalytic Enantioselective Synthesis of Protected à,à-Disubstituted à-Amino Acid Derivativ
PubMed:
Kinetic resolution of racemic 2,3-allenoates by organocatalytic asymmetric 1,3-dipolar cycloaddition
PubMed:
Enantioselective iodolactonization of allenoic acids
PubMed:
Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones
PubMed:
Pyridylalanine (pal)-peptide catalyzed enantioselective allenoate additions to N-acyl imines
PubMed:
Multicomponent reaction of imidazo[1,5-a]pyridine carbenes with aldehydes and dimethyl acetylenedicarboxylate or allenoates: a straightforward approach to fully substituted furans
PubMed:
Inhibitors of protein geranylgeranyltransferase I and Rab geranylgeranyltransferase identified from a library of allenoate-derived compounds
PubMed:
Copper-mediated pyrazole synthesis from 2,3-allenoates or 2-alkynoates, amines and nitriles
PubMed:
Beta-iodoallenolates as springboards for annulation reactions
PubMed:
An unexpected role of a trace amount of water in catalyzing proton transfer in phosphine-catalyzed (3 + 2) cycloaddition of allenoates and alkenes
PubMed:
Multicomponent cascade cycloaddition involving tropone, allenoate, and isocyanide: a rapid access to a 7,6,5-fused tricyclic skeleton
PubMed:
Syntheses of spirocyclic oxindole-butenolides by using three-component cycloadditions of isocyanides, allenoates, and isatins
PubMed:
Isocyanide-based multicomponent reactions: concise synthesis of spirocyclic oxindoles with molecular complexity by using a [1,5]-hydrogen shift as the key step
PubMed:
[Influence of serum on certain properties of the methyl ether of dimethylethylallenolic acid]
PubMed:
Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of à-benzylallenoates with ketones
PubMed:
Efficient assembly of chromone skeleton from 2,3-allenoic acids and benzynes
PubMed:
Phosphine-catalyzed domino reaction for the synthesis of conjugated 2,3-dihydrofurans from allenoates and Nazarov reagents
PubMed:
Studies on the tandem reaction of 4-Aryl-2,3-allenoates with organozinc reagents: a facile route to polysubstituted naphthols
PubMed:
Synthesis of strained tricyclic beta-lactams by intramolecular [2+2] cycloaddition reactions of 2-azetidinone-tethered enallenols: control of regioselectivity by selective alkene substitution
PubMed:
Dual reactivity pattern of allenolates "on water": the chemical basis for efficient allenolate-driven organocatalytic systems
PubMed:
Catalytic enantioselective alkylative aldol reaction: efficient multicomponent assembly of dialkylzincs, allenic esters, and ketones toward highly functionalized delta-lactones with tetrasubstitute
PubMed:
Organocatalysis "on water". Regioselective [3 + 2]-cycloaddition of nitrones and allenolates
PubMed:
Metal-free access to fully substituted skipped diynes. An efficient chemodifferentiating A2BB' 4CR manifold
PubMed:
The asymmetric catalytic aldol reaction of allenolates with aldehydes using n-fluoroacyl oxazaborolidine as the catalyst
PubMed:
Intramolecular allenolate acylations in studies toward a synthesis of FR182877