(3S)-3-Hydroxycyclocitral (BioCAD00000000564)

plant natural products

Metabolite Card

Chinese Name: 羟基-β-环柠檬醛
Formula: C10H16O2 (168.115)
SMILES: 

[H][C@@]1(O)CC(C)=C(C=O)C(C)(C)C1

Synonyms [en]

(3S)-3-hydroxycyclocitral; 3beta-hydroxy-beta-cyclocitral; SCHEMBL10452597; (3S)-hydroxy-beta-cyclocitral; CHEBI:53167; C19731

Reviewed

Last reviewed on 2026-04-16.

Cite this Page

(3S)-3-Hydroxycyclocitral. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/3S_3-Hydroxycyclocitral (retrieved 2026-08-20) (CAD Registry RN: BioCAD00000000564). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

(3s)-3-hydroxycyclocitral, also known as 3beta-hydroxy-beta-cyclocitral, is a member of the class of compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl) (3s)-3-hydroxycyclocitral is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (3s)-3-hydroxycyclocitral can be found in a number of food items such as garden tomato (variety), malabar plum, lime, and pot marjoram, which makes (3s)-3-hydroxycyclocitral a potential biomarker for the consumption of these food products.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 138-55-6
  • PubChem: 13374320
  • PubChem: 25201359
  • ChEBI: ChEBI:53167
  • HMDB: HMDB0303972
  • KEGG: C19731
  • BioCyc: CPD-8661
  • Metlin: METLIN_73322
  • Coconut NaturalProduct: CNP0179468.1
  • PMHub: MS000027390
  • metaboanalyst: 7fbafdd8b8c33e75d59e0c0b64a66063
  • metaboanalyst: ee4b542993cbddb58556a1181928f69a
  • HERB: HBIN039885

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09603 1.13.11.84 zeaxanthin:oxygen 7',8'-oxidoreductase (bond-cleaving)
KEGG:R10843 1.13.11.84 zeaxanthin:oxygen oxidoreductase (7,8-cleaving)
KEGG:R10844 1.13.11.84 beta-citraurin:oxygen oxidoreductase (7,8-cleaving)
KEGG:R12136 C19731<=>C17055
Rhea:RHEA:26398 1.13.11.84 all-trans-zeaxanthin + 2 O2 => crocetin dialdehyde + 2 3β-hydroxy-β-cyclocitral
Rhea:RHEA:26399 1.13.11.84 crocetin dialdehyde + 2 3β-hydroxy-β-cyclocitral => all-trans-zeaxanthin + 2 O2
Rhea:RHEA:26400 1.13.11.84 all-trans-zeaxanthin + 2 O2 <=> crocetin dialdehyde + 2 3β-hydroxy-β-cyclocitral
Rhea:RHEA:43593 all-trans-zeaxanthin + O2 => 3β-hydroxy-β-cyclocitral + (3R)-3-hydroxy-8'-apo-β-carotenal
Rhea:RHEA:43594 3β-hydroxy-β-cyclocitral + (3R)-3-hydroxy-8'-apo-β-carotenal => all-trans-zeaxanthin + O2
Rhea:RHEA:43595 all-trans-zeaxanthin + O2 <=> 3β-hydroxy-β-cyclocitral + (3R)-3-hydroxy-8'-apo-β-carotenal
Rhea:RHEA:43597 (3R)-3-hydroxy-8'-apo-β-carotenal + O2 => crocetin dialdehyde + 3β-hydroxy-β-cyclocitral
Rhea:RHEA:43598 crocetin dialdehyde + 3β-hydroxy-β-cyclocitral => (3R)-3-hydroxy-8'-apo-β-carotenal + O2
Rhea:RHEA:43599 (3R)-3-hydroxy-8'-apo-β-carotenal + O2 <=> crocetin dialdehyde + 3β-hydroxy-β-cyclocitral
BioCyc:RXN-8469 1.13.11.84 CPD1F-130 + 2 OXYGEN-MOLECULE --> CPD-21154 + 2 CPD-8661
BioCyc:RXN-15979 CPD1F-130 + OXYGEN-MOLECULE --> CPD-17216 + CPD-8661
BioCyc:RXN-8477 2.4.1.- CPD-12575 + CPD-8661 --> PROTON + CPD-8668 + UDP
BioCyc:RXN-15980 CPD-17216 + OXYGEN-MOLECULE --> CPD-21154 + CPD-8661
Rhea:RHEA:26397 [26397] all-trans-zeaxanthin + 2 O2 = crocetin dialdehyde + 2 3beta-hydroxy-beta-cyclocitral
Rhea:RHEA:43596 [43596] (3R)-3-hydroxy-8'-apo-beta-carotenal + O2 = crocetin dialdehyde + 3beta-hydroxy-beta-cyclocitral
Rhea:RHEA:43592 [43592] all-trans-zeaxanthin + O2 = 3beta-hydroxy-beta-cyclocitral + (3R)-3-hydroxy-8'-apo-beta-carotenal
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Mass Spectrum
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