Skip to main content

Retinoic acid (ATRA)

ADVERTISEMENT
Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid
State
State

At room temperature, retinoic acid is typically in a solid state.

Melting point (Celsius)
184.00
Melting point (Kelvin)
457.00
Boiling point (Celsius)
575.60
Boiling point (Kelvin)
848.80
General information
Molecular weight
300.44g/mol
Molar mass
300.4410g/mol
Density
1.2000g/cm3
Appearence

Retinoic acid typically appears as a pale yellow to light orange crystalline powder. It is sensitive to air, light, and heat, which may alter its appearance over time.

Comment on solubility

Solubility Characteristics

The compound (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid presents an intriguing case when it comes to its solubility profile. Generally, the solubility of organic compounds is heavily influenced by their molecular structure, which includes factors such as polarity and the presence of functional groups.

Specifically, the solubility can be evaluated based on the following key points:

  • Polarity: The presence of a carboxylic acid group (-COOH) in the compound contributes to its potential polar character, which typically enhances solubility in polar solvents like water.
  • Hydrocarbon Structure: The polycyclic nature and hydrocarbon segments may lead to increased hydrophobicity, which could limit solubility in polar solvents but enhance solubility in non-polar solvents such as hexane or toluene.
  • Hydrogen Bonding: The ability of the carboxylic acid to form hydrogen bonds can significantly influence solubility in water, allowing for better dissolution under the right conditions.

Although the exact solubility parameters are not extensively documented in literature, it is reasonable to hypothesize that:

  1. The compound may be more soluble in polar organic solvents due to the functional groups present.
  2. It may show limited solubility in non-polar solvents while still being able to dissolve to some extent, indicative of a balance between hydrophobic and hydrophilic properties.

As a summary, the solubility of this compound can be characterized as:

  • Potentially high in polar solvents due to the carboxylic group,
  • Moderate in non-polar solvents owing to its hydrocarbon framework.

Understanding the solubility of this compound is important for its application across different fields, from pharmaceuticals to materials science.

Interesting facts

Exciting Insights into (1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid

(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid is a complex organic compound that belongs to the class of phenanthrene derivatives. This compound exhibits fascinating characteristics and potential applications in various scientific fields. Here are some interesting facts:

  • Synthetic Pathways: The synthesis of this compound often involves intricate multi-step reactions, showcasing the creativity and precision required in organic chemistry.
  • Biological Relevance: Compounds similar to this one are studied for their biological activities, particularly in the field of pharmacology, where they may exhibit anti-inflammatory or anti-cancer properties.
  • Structural Complexity: Its unique tetrahydro structure contributes to a rich stereochemistry, making it a subject of interest for stereoisomer research and chiral synthesis.
  • Applications: The presence of functional groups like the carboxylic acid moiety could make this compound useful in the development of new materials or pharmaceuticals.
  • Research Opportunities: This compound is a potential candidate for continued research into natural product synthesis and could lead to discoveries in medicinal chemistry.

In summary, (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid stands out not only for its complex structure but also for its potential implications in both research and application realms. As a chemical scientist, exploring such compounds grants us a deeper understanding of nature's building blocks and paves the way for innovative solutions in health and technology.

Synonyms
7-OXODEHYDROABIETIC ACID
18684-55-4
I8PNL8FLID
7-ketodehydro-abietic acid
Podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-
(1R,4aS,10aR)-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-, (1R,4aS,10aR)-
7-Ketodehydroabietic acid
UNII-I8PNL8FLID
BRN 3216723
7-oxocallitrisic acid
13-Isopropyl-7-oxopodocarpa-8,11,13-trien-15-oic acid
4-10-00-02942 (Beilstein Handbook Reference)
CHEMBL597919
orb1691413
SCHEMBL3212768
DTXSID5075074
MSK162040
AKOS027324385
FS-8481
DA-60583
PD207163
HY-133620
CS-0128446
H26716
EN300-6733727
Q27280582
(1R,4AS,10AR)-1,4A-DIMETHYL-9-OXO-7-(PROPAN-2-YL)-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE-1-CARBOXYLIC ACID
7-Oxodehydroabietic acidPodocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-; 7-Ketodehydroabietic acid; 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-, (1R,4aS,10aR)-