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Sigma-Aldrich

Abietic acid

technical, ~75% (GC)

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Synonym(s):
7,13-abietadien-18-oic acid, Abietate, L-Abietic acid, Rosin acid, Sylvic acid, sylvic acid
Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
Molecular Weight:
302.45
Beilstein:
2221451
EC Number:
MDL number:
eCl@ss:
32150233
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

Assay

~75% (GC)

form

solid

optical activity

[α]20/D −85±10°, c = 1% in ethanol

mp

139-142 °C (lit.)
150-165 °C

storage temp.

2-8°C

SMILES string

CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(O)=O)[C@H]2CC1

InChI

1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1

InChI key

RSWGJHLUYNHPMX-ONCXSQPRSA-N

Gene Information

human ... TNF(7124)

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Application

Abietic acid can be used as a precursor in the preparation of:       
  • Epoxy and petrochemical curing agents.
  •  Dehydroabietic acid derivatives as potential antitumor, antimycotic, and antiviral agents.

It can also be used as a starting material in the total synthesis of:
  • (−)-triptonide and (−)-triptolide as potent antitumor and immunosuppressant agents       
  • quinone (−)-12-deoxyroyleanone as antileishmanial agent       
  • abietic acid-derived catechol (methyl 11,12-dihydroxyabietate-8,11,13-trien-18-oate, MDTO) as a potential antioxidant agent

Other Notes

Starting material for natural product synthesis; Epoxidation with MCPBA

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis and biological evaluation of dehydroabietic acid derivatives.
Gonzalez M A, et al.
European Journal of Medicinal Chemistry, 45(2), 811-816 (2010)
G. Buchbauer et al.
Scientia Pharmaceutica, 53, 173-173 (1985)
Structural effects on the bioactivity of dehydroabietic acid derivatives
Gigante B, et al.
Planta Medica, 68(08), 680-684 (2002)
Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers
Zapata B, et al.
MedChemComm, 4(9), 1239-1246 (2013)
Antioxidant activity of a catechol derived from abietic acid
Justino GC, et al.
Journal of Agricultural and Food Chemistry, 54(2), 342-348 (2006)

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