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Retinoic acid

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Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
State
State

At room temperature, retinoic acid is a solid. It needs to be handled carefully, as it can undergo degradation if exposed to heat, air, or light.

Melting point (Celsius)
183.00
Melting point (Kelvin)
456.00
Boiling point (Celsius)
494.00
Boiling point (Kelvin)
767.00
General information
Molecular weight
300.44g/mol
Molar mass
300.4410g/mol
Density
0.9470g/cm3
Appearence

Retinoic acid usually appears as a yellow to light orange crystalline powder. It is known to be photosensitive, meaning its color may change upon exposure to light.

Comment on solubility

Solubility of 3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

The solubility of 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid (C20H28O2) can be quite complex due to its unique molecular structure. Here are some key points regarding its solubility:

  • Solvent Compatibility: This compound is likely to exhibit higher solubility in organic solvents due to its hydrophobic hydrocarbon chains, which do not favor aqueous environments.
  • Temperature Dependency: Solubility often increases with temperature; thus, heating the solvent may improve the dissolution of this compound.
  • pH Influence: As a carboxylic acid, the solubility in water may also depend on the pH, where increasing acidity could enhance its solubility through ionization.
  • Miscibility Considerations: The compound may be miscible with oils or non-polar solvents, making it ideal for formulations requiring such attributes.

Remember, the phrase "like dissolves like" applies significantly here—the compatibility of solvents with the compound's polar and non-polar characteristics dictates the solubility behavior. In essence, while this compound shows limited solubility in water, it could be significantly solvated in organic media, highlighting the importance of selecting the appropriate solvent for practical applications.

Interesting facts

Interesting Facts about 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

This fascinating compound is a member of the class of carotenoids, which are pigments found in plants that play a crucial role in photosynthesis. Carotenoids are not only responsible for the vibrant colors of fruits and vegetables but also serve as antioxidants that contribute to human health.


Key Characteristics

  • Biological Importance: Like other carotenoids, this compound likely possesses significant biological functionalities and health benefits, including anti-inflammatory properties.
  • Sources: It can be derived from a variety of natural sources, particularly those rich in pigments, such as carrots, sweet potatoes, and leafy greens.
  • Industrial Applications: Its derivatives are commonly used in the food industry as natural colorants and supplements due to their non-toxic nature.

This compound is a perfect example of nature’s complexity, displaying an intricate structure with multiple double bonds that enhance its reactivity and interaction with light. As noted by many researchers, “the interaction of these compounds with light leads to their vivid coloring and potential health benefits.” The presence of methyl groups in its structure increases stability while also contributing to its characteristic pigmentation.


Applications and Research

  • Health Research: Ongoing studies are investigating the potential of such compounds in cancer prevention and retinal health.
  • Agricultural Benefits: They may play roles in plant health, protecting against pests and UV radiation.

As a chemistry student or scientist, studying this compound opens a gateway to understanding the intersections between natural products, health, and innovation in food science.

Synonyms
CHEBI:26536
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
LGD 100057
Spectrum_001676
SpecPlus_000696
Prestwick0_000256
Prestwick0_000257
Prestwick1_000256
Prestwick1_000257
Spectrum2_001983
Spectrum3_001793
Spectrum4_000901
Isotretinoin EP Impurity C
CBiol_001820
CBiol_001822
CBiol_001824
KBioGR_000051
KBioGR_000215
KBioGR_000220
KBioGR_001362
KBioSS_000051
KBioSS_000215
KBioSS_000220
KBioSS_002156
DivK1c_000903
DivK1c_006792
SPBio_002165
SPBio_002291
SPBio_002293
LGD 1057; NSC 659772; Panretin; Panretyn; Panrexin; Toctino
CHEMBL1235644
KBio1_000903
KBio1_001736
KBio2_000051
KBio2_000215
KBio2_000220
KBio2_002156
KBio2_002619
KBio2_002783
KBio2_002788
KBio2_004724
KBio2_005187
KBio2_005351
KBio2_005356
KBio2_007292
KBio3_000101
KBio3_000102
KBio3_000429
KBio3_000430
KBio3_000439
KBio3_000440
KBio3_002847
NINDS_000903
Bio1_000106
Bio1_000108
Bio1_000110
Bio1_000595
Bio1_000597
Bio1_000599
Bio1_001084
Bio1_001086
Bio1_001088
Bio2_000051
Bio2_000215
Bio2_000220
Bio2_000531
Bio2_000695
Bio2_000700
HMS3266L03
HMS3369K04
HMS3371C15
HMS3654B21
HMS3655M15
HMS3744G21
HMS3869E03
HMS3872L03
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2Z,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-Trimethyl-1-Cyclohexenyl)Nona-2,4,6,8-Tetraenoic Acid
AKOS030228441
AB03039
NCGC00017280-22
NCGC00094358-17
NCI60_000538
SY030154
DB-071617
NS00077181
Q27109903
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,6,8-tetraenoic acid