CAS 127-27-5 | Pimaric acid | CAS Number 127-27-5

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127-27-5 | Pimaric acid

CAS No: 127-27-5 Catalog No: AG0038AY MDL No:MFCD01632486

Product Description

Catalog Number:

AG0038AY

Chemical Name:

Pimaric acid

CAS Number:

127-27-5

Molecular Formula:

C20H30O2

Molecular Weight:

302.4510

MDL Number:

MFCD01632486

IUPAC Name:

(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

InChI:

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1

InChI Key:

MHVJRKBZMUDEEV-APQLOABGSA-N

SMILES:

C=C[C@]1(C)CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O

UNII:

88R98Z71NI

NSC Number:

2956

Properties

Complexity:

534

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

302.225g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

302.458g/mol

Monoisotopic Mass:

302.225g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

37.3A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

5.5

Literature

Title	Journal
Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases.	Plant physiology 20130201
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.	Chemico-biological interactions 20120830
Variations in wood burning organic marker concentrations in the atmospheres of four European cities.	Journal of environmental monitoring : JEM 20120801
Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay.	Fitoterapia 20120701
4-epi-Pimaric acid: a phytomolecule as a potent antibacterial and anti-biofilm agent for oral cavity pathogens.	European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20120201
Induction of isoprenyl diphosphate synthases, plant hormones and defense signalling genes correlates with traumatic resin duct formation in Norway spruce (Picea abies).	Plant molecular biology 20111201
[Diterpenoids from Chinese eaglewood].	Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110801
Cerumen of Australian stingless bees (Tetragonula carbonaria): gas chromatography-mass spectrometry fingerprints and potential anti-inflammatory properties.	Die Naturwissenschaften 20110401
On benzofuroindole analogues as smooth muscle relaxants.	Journal of biomedicine & biotechnology 20110101
Subgroup 4 R2R3-MYBs in conifer trees: gene family expansion and contribution to the isoprenoid- and flavonoid-oriented responses.	Journal of experimental botany 20100901
Bioactive diterpenes from the aerial parts of Anisochilus harmandii.	Planta medica 20100501
Immunotherapy of brain cancers: the past, the present, and future directions.	Clinical & developmental immunology 20100101
1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodeca-hydro-phenanthrene-1-carboxylic acid.	Acta crystallographica. Section E, Structure reports online 20090501
Molecular mechanisms of paraptosis induction: implications for a non-genetically modified tumor vaccine.	PloS one 20090101
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.	European journal of pharmacology 20081228
Design, synthesis and characterization of podocarpate derivatives as openers of BK channels.	Bioorganic & medicinal chemistry letters 20081001
Pimaradienoic acid inhibits vascular contraction and induces hypotension in normotensive rats.	The Journal of pharmacy and pharmacology 20080401
Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.	Journal of environmental monitoring : JEM 20080301
Human monocytes kill M-CSF-expressing glioma cells by BK channel activation.	Laboratory investigation; a journal of technical methods and pathology 20070201
Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus lusitanica Mill. from Cameroon.	Journal of ethnopharmacology 20060116
Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid.	The Journal of pharmacy and pharmacology 20050801
Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb.	Archives of pharmacal research 20050101
Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.	Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.	Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20041101
Evidence for the mechanisms underlying the effects of pimaradienoic acid isolated from the roots of Viguiera arenaria on rat aorta.	Pharmacology 20040101
Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers.	Bioorganic & medicinal chemistry letters 20031117
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.	Molecular pharmacology 20021001
Pimarane diterpene from Viguiera arenaria (Asteraceae) inhibit rat carotid contraction.	Fitoterapia 20021001
Antimicrobial diterpenes from the stem bark of Mitrephora celebica.	Fitoterapia 20020801
Reactivity of Trametes laccases with fatty and resin acids.	Applied microbiology and biotechnology 20010401