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Dietary Monoterpenoids

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Handbook of Dietary Phytochemicals

Abstract

A great number of foods, vegetables, fruits, and beverages contain various types of monoterpenoids and their related compounds. This chapter summarizes the distribution of monoterpenoids in dietary foods, vegetables, fruits, beverages, and processed foods, and their biological activity, effects, and application to our health, as well as metabolic pathways of several monoterpenoids in mammals.

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Correspondence to Yoshinori Asakawa .

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The Names of Dietary Monoterpenpids and -Their Structure Numbers

The Names of Dietary Monoterpenpids and -Their Structure Numbers

A:

 

Actinidin

(1)

Actinidiolide

(2)

Actinidiolide (Dihydro-)

(3)

Actinidol

(4)

Artemisia ketone

(5)

Artemisia ketone (Iso-)

(6a)

Artemisia triene

(6b)

Artemisyl acetate

(7)

Artemisia alcohol

(8)

Ascaridole

(9)

Ascaridole (Dihydro-)

(10)

Ascaridole (E-Iso-)

(11a)

Ascaridole (Z-Iso-)

(11b)

B:

 

Bornane

(12)

Borneol

(13)

Bornyl formate

(14)

Bornyl acetate

(15)

Bornyl propanoate

(16a)

Bornyl iso-butyrate

(16b)

Bornyl angelate

(16c)

Bornyl isovalerate

(17)

Bornyl hexanoate

(18)

Borneol (Iso-)

(19a)

Bornyl formate (Iso-)

(19b)

Bornyl acetate (Iso-)

(20)

Bornyl isovalerate (Iso-)

(21)

Bornylene

(22)

C:

 

Camphene

(23)

Camphene hydrate

(24)

Camphenillol (3-Methyl-)

(25)

Camphenilone

(26)

Campholenol (α-)

(27)

Campholenal (α-)

(28)

Camphor

(29)

Carene (Δ2-)

(30)

Carene (Δ3)

(31)

Carene epoxide (Δ2-)

(32)

Carene-4-ol [3(10)-]

(33)

Carvacrol

(34)

Carvacrol methyl ether

(35)

Carvenone

(36)

Carveol (Dihydro-)

(37)

Carveol (E-)

(38a)

Carveyl acetate (E-)

(38b)

Carveol (Z-)

(39a)

Carveyl acetate (Z-)

(39b)

Carveol (Iso-)

(40)

Carvomenthone

(41)

Carvone

(42)

Carvone (Dihydro-)

(43)

Carvone oxide

(44)

Carvotanacetol

(45)

Carvotanacetone

(46)

Chrysanthenol

(47)

Chrysanthenyl acetate (E-)

(48)

Chrysanthenyl acetate (Z-)

(49)

Chrysanthenone (E-)

(50)

Cineole (1,4-)

(51)

Cineole (1,8-)

(52)

Cineole (2,3-Dehydro-1,8-)

(53)

Citral

[(Geraniol (94) & Nerol (234b)]

Citral (E-iso-)

[(Iso-geranial (113a) & Iso-neral (232)]

Citronellal (Dihydro-)

(54)

Citronellal (β-)

(55)

Citronellic acid

(56)

Citronellate (Methyl)

(57)

Citronellol

(58)

Citronellyl acetate

(59)

Citronellyl formate

(60a)

Citronellyl propanoate

(60b)

Citronellyl butanoate

(61)

Citronellyl isobutyrate

(62)

Citronellyl 2-methylbutyrate

(63)

Citronellyl pentanoate

(64)

Citronellyl hexanoate

(65)

Citronellyl heptanoate

(66)

Cryptone

(67)

Cumene

(68a)

Cumenol

(68b)

Cumene (Dehydro-)

(69)

Cumin alcohol

(70)

(= p-cymen-7-ol)

 

Cumin aldehyde

(71)

Cumin aldehyde (Dihydro-)

(72)

Cyclocitral (β-)

(73)

Cyclocitral (β-Homo-)

(74)

Cymene (p-Dehydro-)

(75)

Cymene (p-Dihydro-)

(76)

Cymene (o-)

(77)

Cymene (m-)

(78)

Cymene (p-)

(79)

Cymene-7-ol

(70)

(= Cumin alcohol)

 

Cymen-8-ol (p-)

(80)

Cymen-9-ol (p-)

(81)

Cymen-9-ol (m-)

(82)

Cymenol (p-)

(83)

D:

 

Damascenone(β-)

(84)

Damascone

(85)

Dill ether

(86)

E:

 

Egoma ketone (Iso-)

(87a)

Elsholtzia ketone

(87b)

Eucarvone

(87c)

F:

 

Fenchene (α-)

(88)

Fenchyl alcohol (α-)

(89)

Fenchyl acetate (α-)

(90)

Fenchyl alcohol (β-)

(91)

Fenchyl acetate (β-)

(92a)

Fenchone

(92b)

G:

 

Geijerene

(93)

Geranial

(94)

Geranic acid

(95)

Geranate (Methyl)

(96)

Geraniol

(97)

Geranyl formate

(98)

Geranyl acetate

(99)

Geranyl propanoate

(100)

Geranyl butanoate

(101)

Geranyl iso-butanoate

(102)

Geranyl pentanoate

(103)

Geranyl isovalerate

(104)

Geranyl 2-methylbutanoate

(105)

Geranyl tiglate

(106)

Geranyl hexanoate

(107)

Geranyl heptanoate

(108)

Geranyl octanoate

(109)

Geranyl benzoate

(110)

Geranyl acetone

(111)

Geraniol (Hydroxy-)

(112)

Geranial (Iso-)

(113a)

Geraniol (β-Iso-)

(113b)

Geranyl acetate (α-Cyclo-)

(114)

Geyrene

(115)

I:

 

Ionol (β-)

(116)

Ionone (3-Oxo-α-)

(117)

Ionone (3-Oxo-β-)

(118)

Ionone (4-Oxo-α-)

(119)

Ionone (α-)

(120)

Ionone (α-Dihydro-)

(121)

Ionone (β-)

(122)

Ionone (β-4-Hydroxy-)

(123)

Ionone (β-5,6-Epoxide)

(124)

Ionone (β-Dihydro-)

(125)

Ionone (δ-Dihydro-β-)

(126)

Iridodiol (Dehydro-)

(127a)

Iridodial (Dehydro-)

(127b)

Iridomyrmecin

(128)

Iridomyrmecin (Iso-)

(129)

Iron (α-)

(130a)

Iron (β-)

(130b)

Iron (γ-)

(130c)

Isophorone

(131)

J:

 

Jasmine lactone

(132)

Jasmone (Z-)

(133)

Jasmonate (Methyl)

(134)

L:

 

Lavandulal

(135)

Lavandulol

(136)

Lavandulyl acetate

(137)

Lavandulyl pentanoate

(138)

Lavandulyl 2-methylbutanoate

(139)

Lavandulyl tiglate

(140)

Lavandulol (Tetrahydro-)

(141)

Lilac alcohol a

(142)

Lilac alcohol b

(143)

Lilac alcohol c

(144)

Lilac alcohol d

(145)

Lilac aldehyde 1

(146)

Lilac aldehyde 2

(147)

Lilac aldehyde 3

(148)

Lilac aldehyde 4

(149)

Lilac alcohol formate 1

(150)

Lilac alcohol formate 2

(151)

Limonene

(152)

Limonene (Iso-)

(153)

Limonene 1,2-oxide (E-)

(154a)

Limonene 1,2-oxide (Z-)

(154b)

Limonene diol

(155)

Limonene-10-ol

(156)

Limonene-4-ol

(157)

Linalool

(158)

Linalool (7E-8-hydroxy-)

(159a)

Linalool (7Z-8-Hydroxy-)

(159b)

Linalyl 8-acetate

(160)

Linalool (8-Hydoxydihydro-)

(161)

Linalool (Dihydro-)

(162)

Linalool hydrate

(163)

Linalool oxide (E-: furanoid)

(164a)

Linalool oxide (Z-: furanoid)

(164b)

Linalool oxide (E-: pyranoid)

(165a)

Linalool oxide (Z-: pyranoid)

(165b)

Linalool oxide (β-)

(166)

Linalyl formate

(167)

Linalyl acetate

(168)

Linalyl propanoate

(169)

Linalyl butanoate

(170)

Linalyl pentanoate

(171)

Linalyl iso-valerate

(172)

Linalyl senecioate

(173)

Linalyl hexanoate

(174)

M:

 

Matatabiol (Allo-)

(175a)

Matatabiol (Neo-)

(175b)

Matatabi diether (5-Hydroxy-)

(176)

Matatabi diether (7-Hydroxy-)

(177)

Matatabi ether

(178)

Matatabi diether

(179)

Matatabi lactone

(180)

Menthene (2-)

(181)

Menthofuran

(182a)

p-Mentha-3,9-oxide

(182b)

Menthol

(183)

Menthyl acetate

(184)

Menthol (8-Hydoxy- neo-)

(185)

Menthol (Iso-)

(186a)

Menthol (Iso-) acetate

(186b)

Menthol (Neo-)

(187)

Menthol (Neo-iso-)

(188a)

Menthol (Neo-iso-) acetate

(188b)

Menthone

(189)

Menthone (Iso-)

(190)

Myrcene

(191)

Myrcenol

(192)

Myrtanal

(193)

Myrtanol (E-)

(194a)

Myrtanol (Z-)

(194b)

Myrtenal

(195)

Myrtenol

(196)

Myrtenyl acetate

(197)

Myrtenyl isovalerate

(198)

Myrtenol (Dihydro-)

(199)

p-Menth-2-en-7-ol (E-)

(200)

p-mentha-1(7),8-diene

(201)

m-Mentha-1(7),8-diene

(202)

p-Mentha-1(7),8-dien-2-ol (E-)

(203a)

p-Mentha-1(7),8-dien-2-ol (Z-)

(203b)

p-Mentha-1(7),8-dien-2-yl-

(203c)

acetate (Z-)

 

p-Mentha-1,3,8-triene

(204)

p-Menth-1-en-8-ol

(205)

p-Menth-1-en-9-ol

(206)

p-Menth-1-en-9-yl acetate

(207)

p-Mentha-2,4(8)-diene

(208)

p-Mentha-2,8-dien-1-ol (E-)

(209a)

p-Mentha-2,8-dien-1-ol (Z-)

(209b)

p-Mentha-2,8-dien-1-yl acetate

(210)

p-Menth-2-en-1-ol (E-)

(211a)

p-Menth-2-en-1-ol (Z-)

(211b)

p-Menth-4(8)-en-9-ol

(212)

p-Mentha-1(7),2-dien-8-ol

(213)

p-Mentha-1(7),2-diene

(214)

p-Mentha-1,3-dien-7-ol

(215)

p-Mentha-1,4,8-triene

(216)

p-Mentha-1,5-dien-9-ol

(217)

p-Mentha-1,8-dien-4-ol

(218a)

p-Mentha-1,8-dien-9-ol

(218b)

p-Mentha-2,8-diol (E-)

(219)

p-Menth-1-en-3-one

(220)

p-Menth-1-ene

(221a)

p-Mentha-3,8-diene

(221b)

p-Menth-1-en-8-al

(221c)

p-Menth-1-en-9-al

(221d)

p-Menth-6-en-3-one

(221e)

p-Menth-3-en-2-ol

(222)

p-Menth-3-en-7-ol

(223)

N:

 

Naginata ketone

(224)

Nepetalactone(Neo-)

(225)

Nepetalactone (Dihydro-)

(226)

Nepetalactone (Iso-dihydro-)

(227)

Nepetalactone (E,Z-)

(228)

Nepetalactone (Z,E)

(229)

Nepetalic acid

(230)

Nepetalic anhydride

(231)

Neral (Iso-)

(232)

Neric acid

(233)

Neral

(234a)

Nerol

(234b)

Neryl formate

(235)

Neryl acetate

(236)

Neryl iso-butanoate

(237a)

Neryl iso-valerate

(237b)

Neryl hexanoate

(238)

Nerol (Hydroxy-)

(239)

Neryl acetone

(240)

Neryl oxide

(241)

Nopol

(242)

Norpinene (3,6,6-Trimethyl-2-)

(243)

O:

 

Ocimene (Neo-allo-)

(244)

Ocimene (E-allo-)

(245)

Ocimene (Z-allo-)

(246)

Ocimenol (Z-β-)

(247)

Ocimenone (E-β-)

(248)

Ocimenone (Z-β-)

(249)

Ocimene (E-β-)

(250)

Ocimene (Z-β-)

(251)

Ocimene (E-dihydro-)

(252)

Ocimene (Z-dihydro-)

(253)

P:

 

Pinene (α-)

(254)

Pinene (β-)

(255)

Phellandrene (α-)

(256)

Phellandrene (b-)

(257)

Pinocarveol (E-)

(258a)

Pinocarveol (Z-)

(258b)

Pinocampheol (=3-pinanol)

(258c)

Pinocarveyl acetate

(259)

Pinocarvone

(260)

Pinocamphone (E-)

(261)

Piperitol (E-)

(262)

Piperitol (Z-)

(263)

Piperityl acetate

(264)

Phellandral (α-)

(265)

Phellandrol

(266)

Pulegone (Z-)

(267)

Pulegone (Z-iso-)

(268)

Pinocamphone (Iso-)

(269)

Phellandren-8-ol (α-)

(270)

Perilla alcohol

(271)

Perillyl acetate

(272)

Perilla ketone

(273)

Perillaldehyde

(274)

Piperitenone

(275)

Piperitenone (Iso-)

(276)

Perillene

(277)

Phellandrene oxide

(278)

Piperitenol (E- iso-)

(279)

Piperitenol (Z-iso-)

(280)

Piperitone

(281)

Piperitone (Iso-)

(282)

Pulegol (Iso-)

(283)

Pulegol (Neo-iso-)

(284)

Piperitenone oxide (Z-)

(285)

Pinene hydrate (E-)

(286)

Pinene hydrate (Z-)

(287)

Pinene oxide (β-)

(288)

Piperitone oxide (Z-)

(289)

Perilla ketone (Iso-)

(290)

R:

 

Rose oxide (E-)

(291)

Rose oxide (Z-)

(292)

S:

 

Sabinene (Dehydro-)

(293)

Sabinene

(294 & 295)

Sabinene hydrate (E-)

(296)

Sabinene hydrate (Z-)

(297)

Sabinol (E-)

(298)

Sabinyl acetate (E-)

(299)

Sabinol (Z-)

(300)

Santene

(301a)

Santolina triene

(301b)

Shisofuran

(302)

Shisool (E-)

(303)

Shisool (Z-)

(304)

Sylvestrene

(305)

T:

 

Terpinen-1-ol

(306)

Terpinen-4-ol

(307a)

Terpinen-4-yl acetate

(307b)

Terpinene(β-)

(307c)

Terpinene (α-)

(308)

Terpinene (γ-)

(309)

Terpineol (Z-β-)

(310)

Terpinyl acetate (Z-β-)

(311)

Terpineol (α-)

(312)

Terpinyl acetate (α-)

(313)

Terpinyl propanoate (α-)

(314a)

Terpinyl pentanoate (α-)

(314b)

Terpineol (δ-)

(315)

Terpinolene

(316)

Terpinolene (Iso-)

(317)

Terpinolene-4,8-oxide

(318)

Theaspirane

(319)

Theaspirane-A

(320)

Theaspirane-B

(321)

Theaspirone

(322)

Thuja-2,4(10)-diene

(323)

Thujanol (Z-4-)

(324)

Thujanol (Neo-3-)

(325a)

Thujanol acetate (Neo-3-)

(325b)

Thujyl alcohol

(326)

Thujapricin (α-)

(327)

Thujapricin (β-)

(328a)

Thujapricin (γ-)

(328b)

Thujene (α-)

(329)

Thujene (β-)

(330)

Thujone (α-)

(331a)

Thujone (β-)

(331b)

Thujone-2-ol (3-)

(332)

Thymol

(333)

Thymol methyl ether

(334)

Thymoquinone

(335)

Tricyclene

(336)

U:

 

Umbellulone

(337)

Umbellulone (Dihydro-)

(338)

V:

 

Verbanol (E-)

(339a)

Verbenyl acetate (E-)

(339b)

Verbanol (Iso-)

(340a)

Verbanyl acetate (Iso-)

(340b)

Verbenene

(341)

Verbenol (E-)

(342a)

Verbenyl acetate (E-)

(342b)

Verbenol (Z-)

(343)

(=2-pinen-4-ol)

 

Verbenone

(344)

Y:

 

Yomogi alcohol

(345)

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Asakawa, Y. (2021). Dietary Monoterpenoids. In: Xiao, J., Sarker, S.D., Asakawa, Y. (eds) Handbook of Dietary Phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-13-1745-3_17-2

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  • DOI: https://doi.org/10.1007/978-981-13-1745-3_17-2

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  • Publisher Name: Springer, Singapore

  • Print ISBN: 978-981-13-1745-3

  • Online ISBN: 978-981-13-1745-3

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Chapter history

  1. Latest

    Dietary Monoterpenoids
    Published:
    15 October 2020

    DOI: https://doi.org/10.1007/978-981-13-1745-3_17-2

  2. Original

    Dietary Monoterpenoids
    Published:
    01 September 2020

    DOI: https://doi.org/10.1007/978-981-13-1745-3_17-1