pimaric acid
1-phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-
Identification
| Name | pimaric acid |
| IUPAC | 7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid |
| CAS Number | 127-27-5 |
| FDA UNII | 88R98Z71NI |
| Molecular Formula | C20 H30 O2 |
| Molecular Weight | 302.45750000 |
Regulatory
| FDA Mainterm (IAUFC) | 127-27-5 ; PIMARIC ACID |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 218.50 °C. @ 760.00 mm Hg |
| Boiling Point | 413.18 °C. @ 760.00 mm Hg (est) |
| Flash Point | 390.00 °F. TCC ( 198.70 °C. ) (est) |
| logP (o/w) | 6.731 (est) |
| Soluble in | water, 0.09232 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 pimaric acid usage levels up to | not for fragrance use. |
| Recommendation for pimaric acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
dextropimaric acid
(1theta-(1alpha,4abeta,4balpha,7beta,10aalpha))-7-
ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrene carboxylic acid
7-
ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenecarboxylic acid
7-
ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
13b-
methyl-13-vinylpodocarp-8(14)-en-15-oic acid
1-
phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-
pimara-8(14),15-dien-18-oic acid
pimara-8(14),15-dien-19-oic acid
8(14),15-
pimaradien-18-oic acid
(+)-
pimaric acid
dextro-
pimaric acid
podocarp-8(14)-en-15-oic acid, 13β-methyl-13-vinyl- (8CI)
sandaracopimaric acid
1,4a,7-
trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid
usic acid
PubMed:
Retinoic acid receptor agonist activity of naturally occurring diterpenes.
PubMed:
Drug-induced ion channel opening tuned by the voltage sensor charge profile.
PubMed:
Biotransformation of ent-pimaradienoic acid by cell cultures of Aspergillus niger.
PubMed:
Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases.
PubMed:
Effects of ketamine and its metabolites on ion currents in differentiated hippocampal H19-7 neuronal cells and in HEK293T cells transfected with α-hslo subunit.
PubMed:
Assessment of the in vitro and in vivo genotoxic and antigenotoxic effects of pimaradienoic acid in mammalian cells.
PubMed:
Fungal transformation and schistosomicidal effects of pimaradienoic acid.
PubMed:
Variations in wood burning organic marker concentrations in the atmospheres of four European cities.
PubMed:
Pimaric acid from Aralia cordata has an inhibitory effect on TNF-α-induced MMP-9 production and HASMC migration via down-regulated NF-κB and AP-1.
PubMed:
Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay.
PubMed:
[Diterpenoids from Chinese eaglewood].
PubMed:
4-epi-Pimaric acid: a phytomolecule as a potent antibacterial and anti-biofilm agent for oral cavity pathogens.
PubMed:
Cerumen of Australian stingless bees (Tetragonula carbonaria): gas chromatography-mass spectrometry fingerprints and potential anti-inflammatory properties.
PubMed:
1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodeca-hydro-phenanthrene-1-carboxylic acid.
PubMed:
Ent-pimara-8(14), 15-dien-19-oic acid isolated from the roots of Aralia cordata inhibits induction of inflammatory mediators by blocking NF-kappaB activation and mitogen-activated protein kinase pathways.
PubMed:
Design, synthesis and characterization of podocarpate derivatives as openers of BK channels.
PubMed:
SPE and HPLC/UV of resin acids in colophonium-containing products.
PubMed:
Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.
PubMed:
Pimaradienoic acid inhibits vascular contraction and induces hypotension in normotensive rats.
PubMed:
Human monocytes kill M-CSF-expressing glioma cells by BK channel activation.
PubMed:
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.
PubMed:
Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus lusitanica Mill. from Cameroon.
PubMed:
Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid.
PubMed:
Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb.
PubMed:
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.
PubMed:
Evidence for the mechanisms underlying the effects of pimaradienoic acid isolated from the roots of Viguiera arenaria on rat aorta.
PubMed:
Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers.
PubMed:
Pimarane diterpene from Viguiera arenaria (Asteraceae) inhibit rat carotid contraction.
PubMed:
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.
PubMed:
Reactivity of Trametes laccases with fatty and resin acids.
PubMed:
Exposure to dust, resin acids, and monoterpenes in softwood lumber mills.
PubMed:
Enzyme cytochemical responses of mussels (Mytilus edulis) to resin acid constituents of pulp mill effluents.
PubMed:
Isolation and characterization of isopimaric acid-degrading bacteria from a sequencing batch reactor.
PubMed:
Growth, induction, and substrate specificity of dehydroabietic acid-degrading bacteria isolated from a kraft mill effluent enrichment.
PubMed:
Inhibition of platelet aggregation by diterpene acids from Pinus massoniana resin.
PubMed:
Analgesic principles from Aralia cordata Thunb.
PubMed:
Subacute physiological effects of bleached kraft mill effluent (BKME) on the liver of trout, Salmo gairdneri.
PubMed:
Mutagenicity of resin acids identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay.