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Sigma-Aldrich

Abietic acid

technical, ~75% (GC)

Sinónimos:

7,13-abietadien-18-oic acid, Abietate, L-Abietic acid, Rosin acid, Sylvic acid, sylvic acid

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About This Item

Fórmula empírica (notación de Hill):
C20H30O2
Número de CAS:
514-10-3
Peso molecular:
302.45
Beilstein/REAXYS Number:
2221451
EC Number:
208-178-3
MDL number:
MFCD03423567
UNSPSC Code:
12352002
eCl@ss:
32150233
PubChem Substance ID:
329746989
NACRES:
NA.22

grade

technical

Quality Level

100

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
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCL2936
BCCK2368
BCCH3494
BCCF4728
BCCD4341

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(+)-Dehydroabietylamine technical grade, 60%

Sigma-Aldrich

105198

(+)-Dehydroabietylamine

H. Okawara et al.
Tetrahedron Letters, 23, 1087-1087 (1982)
Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (−)-triptolide from (+)-abietic acid.
Alvarez-Manzaneda E, et al.
Tetrahedron, 63(45), 11204-11212 (2007)
Rosin-based acid anhydrides as alternatives to petrochemical curing agents.
Liu X, et al.
Green Chemistry, 11(7), 1018-1025 (2009)
Antioxidant activity of a catechol derived from abietic acid
Justino GC, et al.
Journal of Agricultural and Food Chemistry, 54(2), 342-348 (2006)
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)
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