Chemicals and Drugs

Retinaldehyde

A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.

Chemical Identity

Chemical Information

Molecular Formula
C20H28O
Molecular Weight
284.4 g/mol
CAS Registry No.
564-87-4
IUPAC Name
(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
InChIKey
NCYCYZXNIZJOKI-IOUUIBBYSA-N
SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C\C(=C\C=O)\C)/C
MeSH Unique ID
D012172
Source
PubChem CID 5280490

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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MeSH Record

Synonyms

14 entry terms
  • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenal
  • Axerophthal
  • Retinal
  • Retinene
  • Retinyl Aldehydde
  • Vitamin A Aldehyde
  • Aldehydde, Retinyl
  • Aldehyde, Vitamin A
  • 11-cis-Retinal
  • 11-trans-Retinal
  • all-trans-Retinal
  • 11 cis Retinal
  • 11 trans Retinal
  • all trans Retinal

MeSH Record

Aspects Covered

29 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, deficiency, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

/biosyn /physiol permitted

MeSH Record

History Note

91(75); was see under RETINOIDS 1984-90; was see under VITAMIN A 1968-83

MeSH Hierarchy

Tree Numbers

  1. D02w.047w.850w
  2. D02w.455w.326.271w.665w.202w.495w.690w
  3. D02w.455w.426w.392.368w.367.379.249w.700w.690w
  4. D02w.455w.849w.131w.495w.690w
  5. D02w.455w.849w.291w.605w
  6. D23.767w.261w.700w.690w

AMA Style

References

  1. National Library of Medicine. Retinaldehyde. Medical Subject Headings (MeSH). 2026. Unique ID D012172. http://id.nlm.nih.gov/mesh/2026/D012172
  2. Retinaldehyde. In: Wikipedia. https://en.wikipedia.org/wiki/11-cis_retinal
  3. Retinaldehyde. In: Wikidata. https://www.wikidata.org/wiki/Q17002962
  4. Retinaldehyde. In: PubChem Compound. CID 5280490. https://pubchem.ncbi.nlm.nih.gov/compound/5280490