Abietic acid

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Abietic acid
Abietic acid.svg
Abietic Acid.png
Names
IUPAC name
Abieta-7,13-dien-18-oic acid
Systematic IUPAC name
(1R,4aR,4bR,10aR)-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid
Other names
Abietinic acid; Sylvic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.436 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-173-3
KEGG
PubChem CID
RTECS number
  • TP8580000
UNII
  • 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 Yes check.svgY
    Key: RSWGJHLUYNHPMX-ONCXSQPRSA-N Yes check.svgY
  • InChI=1/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
    Key: RSWGJHLUYNHPMX-ONCXSQPRBK
  • O=C(O)[C@]3([C@@H]2C/C=C1/C=C(\CC[C@@H]1[C@@]2(C)CCC3)C(C)C)C
Properties
C20H30O2
Molar mass 302.458 g·mol−1
AppearanceYellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water). Colorless solid when pure.
Density 1.06 g/mL
Melting point 172–175 °C (342–347 °F; 445–448 K) [1]
Boiling point 250 °C; 482 °F; 523 K
Insoluble [1]
Solubility in other solventsVery soluble in acetone, petroleum ether, Et2O, and ethanol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Abietic acid (also known as abietinic acid or sylvic acid) is a mild organic acid found in coniferous trees.

Contents

It is a commercially important component of paints, soaps, foods, and soldering flux, and is the primary component of resin acid.

Characteristics

Abietic acid is found in pine trees, including:

Pure abietic acid is a colorless solid, but commercial samples are usually a glassy or partly crystalline yellowish solid that melts at temperatures as low as 85 °C (185 °F). [3]

Abietic acid is soluble in alcohols, acetone, and ethers. Its ester or salt is called an abietate. [4]

Abietic acid belongs to the abietane diterpene group of organic compounds derived from four isoprene units.

Preparation

Abietic acid is extracted from tree rosin [5] (via isomerization) and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees.

Resin acids are converted into ester gum by reaction with controlled amounts of glycerol or other polyhydric alcohols.

Uses

Abietic acid has drying properties, and as ester gum is used in paints, varnishes, and lacquers. [3]

It is also used in soaps, for the analysis of resins, and the preparation of metal resinates.

As rosin

Rosin, of which abietic acid is the principal component:

Safety

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<span class="mw-page-title-main">Levopimaric acid</span> Chemical compound

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. Levopimaric acid accounts for about 18 to 25% of pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.

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References

  1. 1 2 Merck Index , 12th Edition, 3. Abietic Acid
  2. "Abietic Acid". Dr. Duke's Phytochemical and Ethnobotanical Databases. Archived from the original on 2015-09-23. Retrieved 13 January 2012.
  3. 1 2 3 Hoiberg, Dale H., ed. (2010). "abietic acid" . Encyclopædia Britannica. Vol. I: A-ak Bayes (15th ed.). Chicago, Illinois: Encyclopædia Britannica Inc. pp.  32. ISBN   978-1-59339-837-8.
  4. 1 2 Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a26_057
  5. G. C. Harris and T. F. Sanderson (1963). "Abietic Acid". Organic Syntheses . 32: 1; Collected Volumes, vol. 4, p. 1.
  6. 1 2 Nutrition, Center for Food Safety and Applied (2022-08-25). "Food Additive Status List". FDA.
  7. El Sayed, F; Manzur, F; Bayle, P; Marguery, MS; Bazex, J (1995). "Contact urticaria from abietic acid". Contact Dermatitis. 32 (6): 361–2. doi:10.1111/j.1600-0536.1995.tb00628.x. PMID   7554886. S2CID   36139468.
  8. Hausen, BM; Krohn, K; Budianto, E (1990). "Contact allergy due to colophony (VII). Sensitizing studies with oxidation products of abietic and related acids". Contact Dermatitis. 23 (5): 352–8. doi:10.1111/j.1600-0536.1990.tb05171.x. PMID   2096024. S2CID   34726630.
  9. Seong-Soo Roh, Moon-Ki Park and Yong-ung Kim (2010). "Abietic Acid from Resina Pini of Pinus Species as a Testosterone 5α-Reductase Inhibitor". J. Health Sci. 56 (4): 451–455. doi: 10.1248/jhs.56.451 .