pimaric acid

1-phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-

CAS: 127-27-5 C20 H30 O2 MW: 302.45750000

Identification

Namepimaric acid
IUPAC7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
CAS Number127-27-5
FDA UNII88R98Z71NI
Molecular FormulaC20 H30 O2
Molecular Weight302.45750000

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for pimaric acid usage levels up tonot for fragrance use.
Recommendation for pimaric acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

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.