alpha-Terpinene (BioCAD00000006390)

saliva plant natural products microbial natural products

Metabolite Card

Formula: C10H16 (136.1252)
SMILES: CC(C)C1=CC=C(C)CC1

Synonyms [en]

alpha-terpinene; Terpilene; p-Mentha-1,3-diene; 1-Isopropyl-4-methyl-1,3-cyclohexadiene; 1-isopropyl-4-methyl-cyclohexa-1,3-diene; alpha-Terpinen

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

alpha-Terpinene. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000006390). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Alpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645 ). ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 4724-89-4
  • CAS Registry Number: 99-86-5
  • PubChem: 7462
  • ChEBI: ChEBI:10334
  • HMDB: HMDB0036995
  • LipidMaps: LMPR0102090026
  • KEGG: C09898
  • BioCyc: CPD-8735
  • NCBI MeSH: gamma-terpinene
  • Wikipedia: Terpinene
  • RefMet: RM0018554
  • MoNA: HMDB0036995_c_ms_101849
  • MoNA: HMDB0036995_c_ms_101850
  • MoNA: JP007119
  • MoNA: JP007398
  • Metlin: METLIN_41113
  • Coconut NaturalProduct: CNP0063000.0
  • Coconut NaturalProduct: CNP0076041.0
  • Coconut NaturalProduct: CNP0164378.0
  • Coconut NaturalProduct: CNP0178656.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09970 4.2.3.115 geranyl-diphosphate diphosphate-lyase (cyclizing, alpha-terpinene-forming)
Rhea:RHEA:32564 4.2.3.115 (2E)-geranyl diphosphate => α-terpinene + diphosphate
Rhea:RHEA:32565 4.2.3.115 α-terpinene + diphosphate => (2E)-geranyl diphosphate
Rhea:RHEA:32566 4.2.3.115 (2E)-geranyl diphosphate <=> α-terpinene + diphosphate
Rhea:RHEA:67413 α-terpinene + 2 reduced [NADPH—hemoprotein reductase] + 2 O2 => carvacrol + 2 oxidized [NADPH—hemoprotein reductase] + 3 H2O + 2 H+
Rhea:RHEA:67414 carvacrol + 2 oxidized [NADPH—hemoprotein reductase] + 3 H2O + 2 H+ => α-terpinene + 2 reduced [NADPH—hemoprotein reductase] + 2 O2
Rhea:RHEA:67415 α-terpinene + 2 reduced [NADPH—hemoprotein reductase] + 2 O2 <=> carvacrol + 2 oxidized [NADPH—hemoprotein reductase] + 3 H2O + 2 H+
BioCyc:RXN-11279 CPD-461 --> CPD-8735 + PPI
BioCyc:RXN-8546 4.2.3.115 GERANYL-PP --> CPD-8735 + PPI
View More
Organism Source

Taxonomy Source

  1. Magnolia biondii [ncbi taxid: 86725]
  2. Magnolia denudata [ncbi taxid: 85856]
  3. Magnolia kobus [ncbi taxid: 54732]
  4. Magnolia salicifolia [ncbi taxid: 3411]
  5. Magnolia sprengeri [ncbi taxid: 86737]
  6. Santalum album [ncbi taxid: 35974]
  7. Aceriphyllum rossii [ncbi taxid: ]
  8. Acmella ciliata [ncbi taxid: 3122487]
  9. Actinomadura hibisca [ncbi taxid: 68565]
  10. Agnorhiza bolanderi [ncbi taxid: 230216]
  11. Akebia quinata [ncbi taxid: 13331]
  12. Akebia trifoliata [ncbi taxid: 155132]
  13. Alligator mississippiensis [ncbi taxid: 8496]
  14. Alphinia galanga [ncbi taxid: ]
  15. Alpinia galanga [ncbi taxid: 94327]
  16. Amomum compactum [ncbi taxid: ]
  17. Amomum krervanh [ncbi taxid: 649195]
  18. Amomum longiligulare [ncbi taxid: ]
  19. Amomum villosum [ncbi taxid: ]
  20. Amomum xanthioides [ncbi taxid: ]
  21. Anastrepha suspensa [ncbi taxid: 28587]
  22. Anaxagorea clavata [ncbi taxid: ]
  23. Anethum graveolens [ncbi taxid: 40922]
  24. Anethum graveolens L. [ncbi taxid: ]
  25. Angelica acutiloba [ncbi taxid: 55605]
  26. Angelica gigas [ncbi taxid: 85712]
  27. Angelica pubescens [ncbi taxid: 312530]
  28. Angelica pubescens f.biserrata [ncbi taxid: ]
  29. Angelica sinensis [ncbi taxid: 165353]
  30. Anthemis aciphylla BOISS.var.discoidea BOISS [ncbi taxid: ]
  31. Araujia sericifera [ncbi taxid: 63463]
  32. Aria pallescens [ncbi taxid: ]
  33. Arnica nevadensis [ncbi taxid: 436208]
  34. Artemisia annua [ncbi taxid: 35608]
  35. Artemisia argyi [ncbi taxid: 259893]
  36. Artemisia capillaris [ncbi taxid: 265783]
  37. Artemisia dracunculus [ncbi taxid: 72341]
  38. Artemisia messerschmidtiana [ncbi taxid: ]
  39. Artemisia monogyna [ncbi taxid: 1903222]
  40. Artemisia montana [ncbi taxid: 669134]
  41. Artemisia princeps [ncbi taxid: 223870]
  42. Asarum heterotropoides [ncbi taxid: 366663]
  43. Asarum sieboldii [ncbi taxid: 76098]
  44. Asiasarum heterotropoides [ncbi taxid: ]
  45. Asiasarum sieboldii [ncbi taxid: ]
  46. Aspergillus caespitosus [ncbi taxid: 176165]
  47. Asterolasia squamuligera [ncbi taxid: 282650]
  48. Astilbe koreana [ncbi taxid: 657399]
  49. Baeckea frutescens L. [ncbi taxid: ]
  50. Bassia butyracea [ncbi taxid: ]
  51. Beyeria brevifolia [ncbi taxid: 2752376]
  52. Boronia muelleri [ncbi taxid: 1764345]
  53. Boswellia carterii [ncbi taxid: ]
  54. Burkholderia cepacia [ncbi taxid: 292]
  55. Bursaria spinosa [ncbi taxid: 105281]
  56. Canabis sativa [ncbi taxid: ]
  57. Cannabis sativa [ncbi taxid: 3483]
  58. Carpesium abrotanoides [ncbi taxid: 119172]
  59. Carum carvi [ncbi taxid: 48032]
  60. Cassia carnaval [ncbi taxid: ]
  61. Catha edulis [ncbi taxid: 123405]
  62. Catharanthus roseus [ncbi taxid: 4058]
  63. Cedrus libani [ncbi taxid: 93692]
  64. Cetraria aculeata [ncbi taxid: 112271]
  65. Chamaecyparis lawsoniana (A. Murray bis) Parl. [ncbi taxid: ]
  66. Chenopodium ambrosioides L. [ncbi taxid: ]
  67. Chloranthus tianmushanensis [ncbi taxid: ]
  68. Chresta sphaerocephala [ncbi taxid: 434639]
  69. Chromolaena odorata [ncbi taxid: 103745]
  70. Chromolaena pulchella [ncbi taxid: ]
  71. Chrysanthemum indicum [ncbi taxid: 146995]
  72. Chrysanthemum morifolium [ncbi taxid: ]
  73. Chrysanthemum x morifolium [ncbi taxid: 41568]
  74. Chrysanthemum zawadskii [ncbi taxid: ]
  75. Cicuta virosa [ncbi taxid: 48109]
  76. Cinnamomum aromaticum [ncbi taxid: 119260]
  77. Cinnamomum illicioides [ncbi taxid: ]
  78. Cinnamomum parthenoxylum [ncbi taxid: ]
  79. Cinnamomum tenuifolium [ncbi taxid: 1755856]
  80. Cistus albidus [ncbi taxid: 335163]
  81. Citrus [ncbi taxid: 2706]
  82. Citrus aurantifolia [ncbi taxid: ]
  83. Citrus aurantium [ncbi taxid: ]
  84. Citrus grandis [ncbi taxid: ]
  85. Citrus hystrix [ncbi taxid: 170989]
  86. Citrus junos [ncbi taxid: 135197]
  87. Citrus maxima [ncbi taxid: 37334]
  88. Citrus medica [ncbi taxid: 171251]
  89. Citrus medica var. sarcodactylis [ncbi taxid: 381790]
  90. Citrus reticulata [ncbi taxid: 85571]
  91. Citrus sinensis [ncbi taxid: 2711]
  92. Citrus spp. [ncbi taxid: ]
  93. Citrus unshiu [ncbi taxid: 55188]
  94. Cladonia evansii [ncbi taxid: 197026]
  95. Clonostachys rosea [ncbi taxid: 29856]
  96. Cnidium officinale [ncbi taxid: ]
  97. Coccus fagi [ncbi taxid: ]
  98. Colchicum macedonicum [ncbi taxid: 225786]
  99. Conoideocrella tenuis [ncbi taxid: 1105321]
  100. Conyza newii [ncbi taxid: ]
  101. Coprosma acerosa [ncbi taxid: 225357]
  102. Coptis deltoidea [ncbi taxid: 261449]
  103. Coriandrum sativum [ncbi taxid: 4047]
  104. Coriandrum sativum L. [ncbi taxid: ]
  105. Cornulaca monacantha [ncbi taxid: 454476]
  106. Corydalis nakaii [ncbi taxid: ]
  107. Cranfillia vulcanica [ncbi taxid: 393586]
  108. Cuminum cyminum L. [ncbi taxid: ]
  109. Curcuma amanda Roxb [ncbi taxid: ]
  110. Curcuma kwangsiensis [ncbi taxid: 136216]
  111. Curcuma longa [ncbi taxid: 136217]
  112. Curcuma phaeocaulis [ncbi taxid: 136218]
  113. Curcuma wenyujin [ncbi taxid: 136221]
  114. Cyanospira rippkae [ncbi taxid: ]
  115. Cymathere triplicata [ncbi taxid: ]
  116. Dalbergia frutescens [ncbi taxid: 450026]
  117. Daucus carota [ncbi taxid: 4039]
  118. Dendrosenecio kilimanjari [ncbi taxid: 109559]
  119. Dicliptera riparia [ncbi taxid: ]
  120. Dillenia papuana [ncbi taxid: 1085409]
  121. Dipterocarpus alatus [ncbi taxid: 340438]
  122. Drosera peltata [ncbi taxid: 4369]
  123. Echinops amplexicaulis [ncbi taxid: 910522]
  124. Elettaria cardamomum [ncbi taxid: 105181]
  125. Elsholtzia ciliata [ncbi taxid: 662901]
  126. Epaltes gariepina [ncbi taxid: 1548596]
  127. Erwinia rhapontici [ncbi taxid: 55212]
  128. Eucalyptus [ncbi taxid: 3932]
  129. Eucalyptus ovata [ncbi taxid: 155760]
  130. Eucalyptus spp. [ncbi taxid: ]
  131. Euphorbia caducifolia [ncbi taxid: 1129975]
  132. Ferula assafoetida [ncbi taxid: ]
  133. Ferula fukanensis [ncbi taxid: 1271630]
  134. Ferula sinkiangensis [ncbi taxid: 1271632]
  135. Ficus elastica [ncbi taxid: 182112]
  136. Ficus formosana [ncbi taxid: 1127366]
  137. Flacourtia inermis [ncbi taxid: 1857402]
  138. Foeniculum vulgare [ncbi taxid: ]
  139. Folium perillae [ncbi taxid: ]
  140. Forsythia suspensa [ncbi taxid: 126418]
  141. Forsythia viridissima [ncbi taxid: 205691]
  142. Fructus amomi [ncbi taxid: ]
  143. Fructus evodiae [ncbi taxid: ]
  144. Fusarium gibbosum [ncbi taxid: 2126134]
  145. Gardenia fosbergii [ncbi taxid: ]
  146. Hansenia weberbaueriana [ncbi taxid: 54724]
  147. Helianthopsis bishopii [ncbi taxid: ]
  148. Homo sapiens [ncbi taxid: 9606]
  149. Houttuynia cordata [ncbi taxid: 16752]
  150. Houttuynia emeiensis [ncbi taxid: ]
  151. Humulus lupulus [ncbi taxid: 3486]
  152. Hypericum papuanum [ncbi taxid: 1137007]
  153. Hypericum perforatum [ncbi taxid: 65561]
  154. Hypselodoris cantabrica [ncbi taxid: ]
  155. Ilex affinis [ncbi taxid: 185489]
  156. Ilex kaushue [ncbi taxid: 1006183]
  157. Illicium difengpi [ncbi taxid: 124772]
  158. Inula thapsoides [ncbi taxid: ]
  159. Isodon kameba [ncbi taxid: ]
  160. Jaspis stellifera [ncbi taxid: ]
  161. Juniperus spp. [ncbi taxid: ]
  162. Kaempferia pulchra [ncbi taxid: 199647]
  163. Kaunia arbuscularis [ncbi taxid: ]
  164. Lactarius scrobiculatus [ncbi taxid: 93011]
  165. Laggera pterodonta [ncbi taxid: 313968]
  166. Laurus nobilis L. [ncbi taxid: ]
  167. Ligusticum chuanxiong [ncbi taxid: 2689076]
  168. Ligusticum sinense [ncbi taxid: ]
  169. Limeum pterocarpum [ncbi taxid: 764827]
  170. Lippia javanica [ncbi taxid: 925357]
  171. Lippia multiflora [ncbi taxid: ]
  172. Lippia ukambensis [ncbi taxid: ]
  173. Liquidambar formosana [ncbi taxid: 63359]
  174. Liquidambar orientalis [ncbi taxid: 63360]
  175. Litsea ceylanica [ncbi taxid: ]
  176. Litsea cubeba [ncbi taxid: 155299]
  177. Lupinus formosus [ncbi taxid: 53227]
  178. Macrocystidia cucumis [ncbi taxid: 182055]
  179. Magnolia biondii [ncbi taxid: 86725]
  180. Magnolia denudata [ncbi taxid: 85856]
  181. Magnolia kobus [ncbi taxid: 54732]
  182. Magnolia liliflora [ncbi taxid: ]
  183. Magnolia liliiflora [ncbi taxid: 3403]
  184. Magnolia salicifolia [ncbi taxid: 3411]
  185. Magnolia sprengeri [ncbi taxid: 86737]
  186. Masla dianthera [ncbi taxid: ]
  187. Melaleuca alternifolia [ncbi taxid: 164405]
  188. Melaleuca leucadendra [ncbi taxid: 164936]
  189. Melaleuca leucadendra L. [ncbi taxid: ]
  190. Mentha arvensis L. [ncbi taxid: ]
  191. Mentha piperita [ncbi taxid: ]
  192. Mentha piperita L. [ncbi taxid: ]
  193. Moringa oleifera [ncbi taxid: 3735]
  194. Mosla chinensis [ncbi taxid: 516065]
  195. Mosla dianthera [ncbi taxid: 1874238]
  196. Murraya exotica [ncbi taxid: 2901850]
  197. Murraya paniculata [ncbi taxid: 43711]
  198. Myristica fragrans [ncbi taxid: 51089]
  199. Nerita albicilla [ncbi taxid: 52928]
  200. Notopterygium incisum [ncbi taxid: ]
  201. Ocimum spp. [ncbi taxid: ]
  202. Odixia angusta [ncbi taxid: 125740]
  203. Origanum majorana [ncbi taxid: 268884]
  204. Oxandra xylopioides [ncbi taxid: 306934]
  205. Palicourea alpina [ncbi taxid: 60103]
  206. Parmelia enteromorpha [ncbi taxid: ]
  207. Peltigera aphthosa [ncbi taxid: 52881]
  208. Pericarpium citri reticulatae viride [ncbi taxid: ]
  209. Persicaria thunbergii [ncbi taxid: 668956]
  210. Petasites tatewakianus [ncbi taxid: 1815966]
  211. Petriella guttulata [ncbi taxid: 70119]
  212. Pheidole pallidula [ncbi taxid: 190770]
  213. Phyllobates aurotaenia [ncbi taxid: 152497]
  214. Pilocarpus affinis pauciflorus [ncbi taxid: ]
  215. Pinus halepensis [ncbi taxid: 71633]
  216. Piper arboreum [ncbi taxid: 130381]
  217. Piper cubeba [ncbi taxid: 405322]
  218. Piper fimbriulatum [ncbi taxid: 425151]
  219. Piper nigrum [ncbi taxid: 13216]
  220. Plagiochila standleyi [ncbi taxid: ]
  221. Platycladus orientalis [ncbi taxid: 58046]
  222. Plectranthus marrubioides [ncbi taxid: ]
  223. Pluchea dioscoridis [ncbi taxid: 264977]
  224. Posoqueria latifolia [ncbi taxid: 58460]
  225. Primula macrophylla [ncbi taxid: 487793]
  226. Prosopis glandulosa [ncbi taxid: ]
  227. Prunus laurocerasus [ncbi taxid: 32242]
  228. Pseudopterogorgia kallos [ncbi taxid: ]
  229. Pteris prolifera [ncbi taxid: ]
  230. Pterocarpus grandiflorus [ncbi taxid: ]
  231. Punica granatum [ncbi taxid: 22663]
  232. Pyrola rotundifolia [ncbi taxid: 13651]
  233. Pyrosoma giganteum [ncbi taxid: ]
  234. Quercus aegilops [ncbi taxid: ]
  235. Quercus coccifera [ncbi taxid: 58335]
  236. Radix chuanxiong [ncbi taxid: ]
  237. Radix et rhizoma anisochili [ncbi taxid: ]
  238. Rhizobium phaseoli [ncbi taxid: 396]
  239. Rhizoma ahemones daddeanae [ncbi taxid: ]
  240. Rhizoma chuanxiong [ncbi taxid: ]
  241. Rhodiola rosea L. [ncbi taxid: ]
  242. Rhodomyrtus tomentosa [ncbi taxid: 98583]
  243. Rosmarinus officinalis [ncbi taxid: ]
  244. Rosmarinus officinalis L. [ncbi taxid: ]
  245. Salix sieboldiana [ncbi taxid: 2878180]
  246. Salvia officinalis [ncbi taxid: 38868]
  247. Salvia xalapensis [ncbi taxid: 2039553]
  248. Sambucus ebulus [ncbi taxid: 28503]
  249. Saussurea lappa [ncbi taxid: ]
  250. Schisandra chinensis [ncbi taxid: 50507]
  251. Scrophularia smithii [ncbi taxid: 1357656]
  252. Securidaca inappendiculata [ncbi taxid: 3091905]
  253. Senecio squalidus [ncbi taxid: 121554]
  254. Senna alexandrina [ncbi taxid: 72402]
  255. Seriphidium cinum [ncbi taxid: ]
  256. Sesbania punicea [ncbi taxid: 543741]
  257. Simira eliezeriana [ncbi taxid: ]
  258. Sinopodophyllum hexandrum [ncbi taxid: 93608]
  259. Solanum lycopersicum [ncbi taxid: 4081]
  260. Solanum torvum [ncbi taxid: 119830]
  261. Stenostomum lucidum [ncbi taxid: 43446]
  262. Stereocaulon sasakii [ncbi taxid: 373710]
  263. Stevia alpina [ncbi taxid: ]
  264. Stoeba extensa [ncbi taxid: ]
  265. Streptomyces althioticus [ncbi taxid: 83380]
  266. Streptomyces fulvoviridis [ncbi taxid: 66891]
  267. Streptomyces violaceochromogenes [ncbi taxid: 67377]
  268. Strophanthus eminii [ncbi taxid: 52859]
  269. Syzygium aromaticum [ncbi taxid: 219868]
  270. Tanacetum annuum [ncbi taxid: ]
  271. Tanacetum santolinoides [ncbi taxid: ]
  272. Tarchonanthus camphoratus [ncbi taxid: 41650]
  273. Taxodium mucronatum [ncbi taxid: 99812]
  274. Tetradenia riparia [ncbi taxid: 992795]
  275. Teucrium polium subsp. polium [ncbi taxid: 1117666]
  276. Thymus quinquecostatus [ncbi taxid: 228974]
  277. Thymus vulgaris [ncbi taxid: 49992]
  278. Trichostema lanceolatum [ncbi taxid: 201523]
  279. Trifolium alexandrium [ncbi taxid: ]
  280. Trifolium pratense [ncbi taxid: 57577]
  281. Trifolium repens [ncbi taxid: 3899]
  282. Trifolium repens L. [ncbi taxid: ]
  283. Tylophora flava [ncbi taxid: ]
  284. Ulva clathrata [ncbi taxid: 99494]
  285. Valeriana jatamansi [ncbi taxid: 59170]
  286. Vitex madiensis [ncbi taxid: 1899206]
  287. Vitis vinifera [ncbi taxid: 29760]
  288. Wunderlichia mirabilis [ncbi taxid: 375931]
  289. Zanthoxylum bungeanum [ncbi taxid: 328401]
  290. Zanthoxylum piperitum [ncbi taxid: 354529]
  291. Zanthoxylum schinifolium [ncbi taxid: 354530]
  292. Zilla spinosa [ncbi taxid: 127626]
  293. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:SPENNELLII_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:NTABACUM_TN90_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:PAXILLARIS_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:POTATO_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:TOMATO_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:PLANT_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:EGGPLANT_PWY-6447 trichome monoterpenes biosynthesis
PlantCyc:MGUTTATUS_PWY-6447 trichome monoterpenes biosynthesis
View All Pathways