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Abietic acid

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Identification
Molecular formula
C20H30O2
CAS number
514-10-3
IUPAC name
(1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid
State
State

At room temperature, abietic acid is typically found as a solid. In its high purity form, it can be crystalline and may transition into a sticky, viscous state at elevated temperatures, particularly above its melting point.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
265.00
Boiling point (Kelvin)
538.15
General information
Molecular weight
302.45g/mol
Molar mass
302.4510g/mol
Density
1.0600g/cm3
Appearence

Abietic acid is a yellowish solid substance. In its pure form, it may appear as a crystalline solid or a viscous liquid, depending on the temperature. This compound is extracted from rosin, the solid form of resin obtained from pines and some other plants, mostly conifers. It is best known for being an ingredient in varnishes and other coatings.

Comment on solubility

Solubility of (1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

The solubility of (1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid can be quite nuanced due to its complex structure. Here are some key points to consider:

  • Polarity: As a carboxylic acid, the compound contains a carboxyl group (-COOH) that typically increases its polarity, enhancing its ability to dissolve in polar solvents like water to some degree.
  • Solvent Compatibility: It may be more soluble in organic solvents such as ethanol, ether, or acetone, which can better accommodate the hydrocarbons and branched groups present in the structure.
  • Hydrophobic Regions: The large hydrophobic aromatic and aliphatic portions of the molecule could reduce solubility in water, favoring organic polarity.
  • Temperature Effects: Increasing temperature tends to increase solubility; thus, heating the solvent may help in dissolving this compound effectively.
  • pH Dependency: The carboxylic acid can ionize in basic conditions, influencing solubility. This could lead to a salt form that is more soluble than the neutral acid.

In summary, while the solubility characteristics of this compound suggest some potential for dissolution in both polar and non-polar environments, they are highly influenced by external factors such as temperature and pH. Understanding these dynamics is crucial for practical applications and investigations involving this complex chemical.

Interesting facts

Interesting Facts about (1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

This compound belongs to a fascinating class of organic compounds known as carboxylic acids, which are prevalent in nature and play significant roles in various biochemical processes. The unique structure of this compound showcases a polycyclic system, featuring a phenanthrene backbone that contributes to its interesting chemical behavior.

Key Characteristics

  • Natural Occurrence: Many carboxylic acids are found in fats, oils, and even in some amino acids, which are the building blocks of proteins.
  • Synthesis: This compound can potentially be synthesized through multi-step organic reactions, making it a great subject for students studying organic chemistry techniques.
  • Applications: Compounds similar to this one are often explored for their potential in pharmaceuticals and biochemistry, particularly in drug development.

The stereochemistry of this compound—indicated by its (R) and (S) configurations—offers a glimpse into the concept of chirality, a critical factor in the activity of many biological molecules. This chirality can affect how the compound interacts with enzymes and receptors in the body, hinting at its potential biological significance.

Interestingly, the presence of the isopropyl and dimethyl substituents can significantly influence the chemical reactivity and physical properties of the molecule, making it a prime candidate for further study. As a chemistry student, exploring such compounds can deepen your understanding of molecular interactions, reaction mechanisms, and the importance of molecular geometry.

In summary, this compound serves as an excellent intersection of organic chemistry, biochemistry, and pharmacology, presenting numerous avenues for exploration and research.

Synonyms
ABIETIC ACID
514-10-3
Sylvic acid
l-Abietic acid
7,13-Abietadien-18-oic acid
Kyselina abietova
13-Isopropylpodocarpa-7,13-dien-15-oic acid
CCRIS 3183
Abietic acid, technical
Abietinic acid
EINECS 208-178-3
NSC 25149
UNII-V3DHX33184
(-)-Abietic acid
CHEBI:28987
AI3-17273
V3DHX33184
NSC-25149
DTXSID7022047
Podocarpa-7,13-dien-15-oic acid, 13-isopropyl-
(1R,4aR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid
(1R,4AR,4BR,10AR)-1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-1-PHENANTHRENECARBOXYLIC ACID
Levamisole resinate
DTXCID202047
1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-, (1R-(1ALPHA,4ABETA,4BALPHA,10A.ALPHA)).-
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl-)-
208-178-3
dtxsid9047831
nocas_47831
Abietate
Rosin Acid
MFCD03423567
Abieta-7,13-dien-18-oic acid
Abietic Acid, >95%
(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
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aR,4bR,10aR)-
NSC25149
(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid
Abietic Acid, 75%
NCGC00166273-01
Colophonium
abieta-7,13-dien-18-oate
Kyselina abietova [Czech]
Abietic acid dimer
15522-12-0
Kolophonium
Highrosin
Shiragiku rosin
Yellow resin
Rondis R
WW Wood rosin
Rosin WW
Hongkong rosin WW
AbietinsA currencyure
Rosin [USP]
Bandis G100
Abietic acid, 90%
Caswell No. 667
BALS 3A
DSSTox_CID_2047
ABIETIC ACID [MI]
DSSTox_RID_82575
DSSTox_GSID_47831
SCHEMBL28888
CHEMBL71893
Podocarpa-7, 13-isopropyl-
EM 3
UNII-88S87KL877
RSWGJHLUYNHPMX-ONCXSQPRSA-
AAA51410
BCP14376
MSK40139
EINECS 232-475-7
Tox21_112386
BDBM50442901
KE 709
NSC154789
Podocarpa-7, 13-isopropyl-, dimer
s5122
AKOS016036412
88S87KL877
Abietic acid, technical, ~75% (GC)
CCG-267495
EPA Pesticide Chemical Code 067205
LMPR0104050001
NSC-154789
(5beta)-abieta-7,13-dien-18-oic acid
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl- )-
AS-35301
DA-50090
NCI60_002007
NS00075578
10248-55-2
C06087
EC 232-475-7
EN300-1699654
Q321068
WLN: L B666 EU GUTJ A1 EY1&1 KVQ K1
C32BF2BB-9F97-4AF5-8F5E-06BC0EA97E83
F8881-8980
Z1954802293
Abietic acidColeonol; colforsina; colforsine; colforsinum; Boforsin
1-Phenanthrenecarboxylic acid,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, [1R-(1.alpha.,4a.beta.,4b.alpha.,10a.alpha.)]-
A9H
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